Process for production of alcohol compound

Description

TECHNICAL FIELD

The present invention relates to a process for production of an alcohol compound.

BACKGROUND ART

For production of 3-(2,6-dichloro-4-benzyloxy)phenoxy)-1-propyl alcohol, there is a known process which comprises reacting 2-bromo-1-ethanol with 2,6-dichloro-4-benzyloxyphenol in N,N-dimethylformamide in the presence of potassium carbonate to produce 2-(2,6-dichloro-4-benzyloxy)phenoxy)-1-ethanol (Patent Document 1 and Patent Document 2).

Patent Document 1: JP-A 9-151172
Patent Document 2: WO2004-099145A2

DISCLOSURE OF THE INVENTION
Problem to be Solved by the Invention

The above process uses N,N-dimethylformamide as a reaction solvent, and therefore, it has a problem that recovery of the solvent after reaction requires energy or disposal of the solvent after reaction put a burden on the environment. Thus, the present invention is to provide a way to solve the problem.

Means for Solving the Problem

The present invention provides a process for production of an alcohol compound represented by the formula (3):

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wherein X₁, X₂, X₃and X₄independently represent a hydrogen atom, a halogen atom or an alkyl group having 1 to 3 carbon atoms, Z represents an oxygen atom or a sulfur atom, R represents an alkyl group, an alkenyl group, an alkynyl group, or an aralkyl group which may be substituted with a halogen atom, and n represents an integer of 2 or 3; which comprises reacting a phenol represented by the formula (1):

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wherein X₁, X₂, X₃, X₄, Z and R are as defined above, with a haloalcohol represented by the formula (2):

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wherein Y represents a chlorine atom or a bromine atom, and n is as defined above, in a biphase system composed of a water-immiscible organic solvent and an aqueous alkali metal hydroxide solution in the presence of a phase-transfer catalyst.

EFFECTS OF THE INVENTION

According to the process of the present invention, the alcohol compound represented by the formula (3) can be produced efficiently with reduced environmental burdens.

BEST MODE FOR CARRYING OUT THE INVENTION

The present invention will be described below.

Substituents represented by X₁, X₂, X₃and X₄in the formulae (1) and (3) are described. Examples of the halogen atom represented by X₁, X₂, X₃or X₄include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. Examples of the alkyl group having 1 to 3 carbon atoms represented by X₁, X₂, X₃or X₄include a methyl group, an ethyl group, an n-propyl group, an iso-propyl group and the like. Preferably Z is an oxygen atom.

In the formulae (1) and (3), examples of the alkyl group represented by R include a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an n-hexyl group and the like.

Examples of the alkenyl group include an allyl group. Examples of the alkynyl group include a propargyl group.

Typical examples of the aralkyl group include a benzyl group. Examples of the aralkyl group substituted with a halogen atom include those having benzene rings in which a hydrogen atom is substituted with a fluorine atom, a chlorine atom, a bromine atom or an iodine atom. Specific examples of the aralkyl group substituted with a halogen atom include, but not limited to, a 2-fluorophenylmethyl group, a 3-fluorophenylmethyl group, a 4-fluorophenylmethyl group, a 2-chlorophenylmethyl group, a 3-chlorophenylmethyl group, a 4-chlorophenylmethyl group, a 2-bromophenylmethyl group, a 3-bromophenylmethyl group, a 4-bromophenylmethyl group, a 2-iodophenylmethyl group, a 3-iodophenylmethyl group and a 4-iodophenylmethyl group. In the aralkyl group substituted with a halogen atom, the substitution position of the halogen atom is not specifically limited. Preferably R is an aralkyl group which may be substituted with a halogen atom. More preferably R is a benzyl group.

Examples of the phenol represented by the formula (1) include 4-methoxyphenol, 4-ethoxyphenol, 4-n-propyloxyphenol, 4-iso-propyloxyphenol, 4-n-butyloxyphenol, 4-sec-butyloxyphenol, 4-tert-butyloxyphenol, 4-n-pentyloxyphenol, 4-n-hexyloxyphenol, 4-(2-propenyloxy)phenol, 4-(2-propynyloxy)phenol, 4-benzyloxyphenol, 4-(2-fluorophenylmethyloxy)phenol, 4-(3-fluorophenylmethyloxy)phenol, 4-(4-fluorophenylmethyloxy)phenol, 4-(2-chlorophenylmethyloxy)phenol, 4-(3-chlorophenylmethyloxy)phenol, 4-(4-chlorophenylmethyloxy)phenol, 4-(4-bromophenylmethyloxy)phenol and 4-(4-iodophenylmethyloxy)phenol.

In the formula (2), Y preferably represents a bromine atom and n preferably represents an integer of 3. Examples of the haloalcohol represented by the formula (2) include 2-chloro-1-ethanol, 3-chloro-1-propanol, 2-bromo-1-ethanol and 3-bromo-1-propanol. Preferred is 3-bromo-1-propanol.

Examples of the water-immiscible organic solvent used in the reaction include hydrocarbon compounds. Specific examples thereof include aliphatic hydrocarbon compounds such as hexane and heptane, aromatic hydrocarbon compounds such as toluene, xylene and monochlorobenzene, and their mixtures. Other examples of the water-immiscible organic solvent include chain ether compounds such as diethyl ether and methyl-tert-butyl ether, and their mixtures. As the water-immiscible organic solvent, preferably hydrocarbon compounds or chain ether compounds are used. From the viewpoint of versatility, toluene is more preferably used.

The amount of the water-immiscible organic solvent used is not specifically limited. From the viewpoint of volume efficiency, the amount of the water-immiscible organic solvent used is usually 0.1 parts by weight to 20 parts by weight per 1 part by weight of the phenol represented by the formula (1).

Examples of the aqueous alkali metal hydroxide solution used in the reaction include aqueous solutions of lithium hydroxide, sodium hydroxide and potassium hydroxide. The amount of the alkaline metal hydroxide used is usually 0.9 mol to 3 mol per 1 mol of the phenol represented by the formula (1). The concentration of alkali metal hydroxide in the aqueous alkali metal hydroxide solution is not specifically limited, and is usually 2% by weight to 10% by weight.

Examples of the phase-transfer catalyst include quaternary ammonium salts such as tetra-n-butylammonium chloride, tetra-n-butylammonium bromide, tetra-n-butylammonium iodide, tetra-n-butylammonium sulfate, triethylbenzylammonium chloride and trioctylmethylammonium chloride, quaternary phosphonium salts such as trimethylphenylphosphonium bromide and pyridinium salts such as n-dodecylpyridinium chloride. When the reaction is performed in the presence of such a phase-transfer catalyst, the alcohol compound represented by the formula (3) is produced in good yield. From the viewpoints of availability and versatility, a tetra-n-butylammonium salt such as tetra-n-butylammonium chloride, tetra-n-butylammonium bromide, tetra-n-butylammonium iodide or tetra-n-butylammonium sulfate is preferably used as the phase-transfer catalyst.

The amount of the phase-transfer catalyst used is not specifically limited. Considering economic efficiency and the like, the phase-transfer catalyst is usually used in an amount of 0.01 mol to 0.2 mol per 1 mol of the phenol represented by the formula (1).

The order of mixing the phenol represented by the formula (1), the haloalcohol represented by the formula (2), the water-immiscible organic solvent, the aqueous alkali metal hydroxide solution and the phase-transfer catalyst is not specifically limited. For example, these materials may be mixed all at once and stirred to react. Alternatively, to an aqueous mixture solution of the phenol and the aqueous alkali metal hydroxide solution may be added dropwise a mixture solution of the haloalcohol and the water-immiscible organic solvent. An aqueous mixture solution of the phenol and the aqueous alkali metal hydroxide solution can be also added dropwise to a mixture solution of the haloalcohol and the water-immiscible organic solvent.

The reaction can be performed at a temperature from a room temperature to a refluxing temperature. The reaction temperature is usually from a room temperature to 100° C. From the viewpoint of a reaction rate, the reaction is preferably performed within the range of 50° C. to 100° C. The reaction time is usually about 10 hours to about 20 hours. Progress of the reaction can be monitored by analyzing the residual amount of the phenol represented by the formula (1) using gas chromatography or liquid chromatography.

After the end of the reaction, a reaction mixture is usually allowed to stand and separated to give an oil layer containing the intended product, the alcohol compound represented by the formula (3). The oil layer can be washed with water. The oil layer also can be neutralized with acidic water such as aqueous sulfuric acid, separated, and washed with water again.

After washing, for example, the obtained oil layer can be concentrated under reduced pressure to remove the organic solvent to give a concentrate of the alcohol compound represented by the formula (3). The concentrate can be further subjected to general purification such as silica gel column chromatography, crystallization and recrystallization, if necessary.

As described above, the intended alcohol compound represented by the formula (3) can be produced efficiently in good yield. Examples of the compound represented by the formula (3) include the following compounds.

(3)

No.
n
X₁
X₂
X₃
X₄
Z
R

1
2
H
H
H
H
O
CH₃

2
2
H
H
H
H
O
CH₂CH₃

3
2
H
H
H
H
O
CH₂CH₂CH₃

4
2
H
H
H
H
O
CH₂Ph

5
2
H
H
H
H
O
CH₂CH═CH₂

6
2
H
H
H
H
S
CH₃

7
2
H
H
H
H
S
CH₂CH₃

8
2
H
H
H
H
S
CH₂CH₂CH₃

9
2
H
H
H
H
S
CH₂Ph

10
2
H
H
H
H
S
CH₂CH═CH₂

11
2
F
F
H
H
O
CH₃

12
2
F
F
H
H
O
CH₂CH₃

13
2
F
F
H
H
O
CH₂CH₂CH₃

14
2
F
F
H
H
O
CH₂Ph

15
2
F
F
H
H
O
CH₂CH═CH₂

16
2
F
F
H
H
S
CH₃

17
2
F
F
H
H
S
CH₂CH₃

18
2
F
F
H
H
S
CH₂CH₂CH₃

19
2
F
F
H
H
S
CH₂Ph

20
2
F
F
H
H
S
CH₂CH═CH₂

21
2
F
Cl
H
H
O
CH₃

22
2
F
Cl
H
H
O
CH₂CH₃

23
2
F
Cl
H
H
O
CH₂CH₂CH₃

24
2
F
Cl
H
H
O
CH₂Ph

25
2
F
Cl
H
H
O
CH₂CH═CH₂

26
2
F
Cl
H
H
S
CH₃

27
2
F
Cl
H
H
S
CH₂CH₃

28
2
F
Cl
H
H
S
CH₂CH₂CH₃

29
2
F
Cl
H
H
S
CH₂Ph

30
2
F
Cl
H
H
S
CH₂CH═CH₂

31
2
F
Br
H
H
O
CH₃

32
2
F
Br
H
H
O
CH₂CH₃

33
2
F
Br
H
H
O
CH₂CH₂CH₃

34
2
F
Br
H
H
O
CH₂Ph

35
2
F
Br
H
H
O
CH₂CH═CH₂

36
2
F
Br
H
H
S
CH₃

37
2
F
Br
H
H
S
CH₂CH₃

38
2
F
Br
H
H
S
CH₂CH₂CH₃

39
2
F
Br
H
H
S
CH₂Ph

40
2
F
Br
H
H
S
CH₂CH═CH₂

41
2
F
CH₃
H
H
O
CH₃

42
2
F
CH₃
H
H
O
CH₂CH₃

43
2
F
CH₃
H
H
O
CH₂CH₂CH₃

44
2
F
CH₃
H
H
O
CH₂Ph

45
2
F
CH₃
H
H
O
CH₂CH═CH₂

46
2
F
CH₃
H
H
S
CH₃

47
2
F
CH₃
H
H
S
CH₂CH₃

48
2
F
CH₃
H
H
S
CH₂CH₂CH₃

49
2
F
CH₃
H
H
S
CH₂Ph

50
2
F
CH₃
H
H
S
CH₂CH═CH₂

51
2
Cl
Cl
H
H
O
CH₃

52
2
Cl
Cl
H
H
O
CH₂CH₃

53
2
Cl
Cl
H
H
O
CH₂CH₂CH₃

54
2
Cl
Cl
H
H
O
CH₂Ph

55
2
Cl
Cl
H
H
O
CH₂CH═CH₂

56
2
Cl
Cl
H
H
S
CH₃

57
2
Cl
Cl
H
H
S
CH₂CH₃

58
2
Cl
Cl
H
H
S
CH₂CH₂CH₃

59
2
Cl
Cl
H
H
S
CH₂Ph

60
2
Cl
Cl
H
H
S
CH₂CH═CH₂

61
2
Cl
Br
H
H
O
CH₃

62
2
Cl
Br
H
H
O
CH₂CH₃

63
2
Cl
Br
H
H
O
CH₂CH₂CH₃

64
2
Cl
Br
H
H
O
CH₂Ph

65
2
Cl
Br
H
H
O
CH₂CH═CH₂

66
2
Cl
Br
H
H
S
CH₃

67
2
Cl
Br
H
H
S
CH₂CH₃

68
2
Cl
Br
H
H
S
CH₂CH₂CH₃

69
2
Cl
Br
H
H
S
CH₂Ph

70
2
Cl
Br
H
H
S
CH₂CH═CH₂

71
2
Cl
CH₃
H
H
O
CH₃

72
2
Cl
CH₃
H
H
O
CH₂CH₃

73
2
Cl
CH₃
H
H
O
CH₂CH₂CH₃

74
2
Cl
CH₃
H
H
O
CH₂Ph

75
2
Cl
CH₃
H
H
O
CH₂CH═CH₂

76
2
Cl
CH₃
H
H
S
CH₃

77
2
Cl
CH₃
H
H
S
CH₂CH₃

78
2
Cl
CH₃
H
H
S
CH₂CH₂CH₃

79
2
Cl
CH₃
H
H
S
CH₂Ph

80
2
Cl
CH₃
H
H
S
CH₂CH═CH₂

81
2
Br
Br
H
H
O
CH₃

82
2
Br
Br
H
H
O
CH₂CH₃

83
2
Br
Br
H
H
O
CH₂CH₂CH₃

84
2
Br
Br
H
H
O
CH₂Ph

85
2
Br
Br
H
H
O
CH₂CH═CH₂

86
2
Br
Br
H
H
S
CH₃

87
2
Br
Br
H
H
S
CH₂CH₃

88
2
Br
Br
H
H
S
CH₂CH₂CH₃

89
2
Br
Br
H
H
S
CH₂Ph

90
2
Br
Br
H
H
S
CH₂CH═CH₂

91
2
Br
CH₃
H
H
O
CH₃

92
2
Br
CH₃
H
H
O
CH₂CH₃

93
2
Br
CH₃
H
H
O
CH₂CH₂CH₃

94
2
Br
CH₃
H
H
O
CH₂Ph

95
2
Br
CH₃
H
H
O
CH₂CH═CH₂

96
2
Br
CH₃
H
H
S
CH₃

97
2
Br
CH₃
H
H
S
CH₂CH₃

98
2
Br
CH₃
H
H
S
CH₂CH₂CH₃

99
2
Br
CH₃
H
H
S
CH₂Ph

100
2
Br
CH₃
H
H
S
CH₂CH═CH₂

101
2
CH₃
CH₃
H
H
O
CH₃

102
2
CH₃
CH₃
H
H
O
CH₂CH₃

103
2
CH₃
CH₃
H
H
O
CH₂CH₂CH₃

104
2
CH₃
CH₃
H
H
O
CH₂Ph

105
2
CH₃
CH₃
H
H
O
CH₂CH═CH₂

106
2
CH₃
CH₃
H
H
S
CH₃

107
2
CH₃
CH₃
H
H
S
CH₂CH₃

108
2
CH₃
CH₃
H
H
S
CH₂CH₂CH₃

109
2
CH₃
CH₃
H
H
S
CH₂Ph

110
2
CH₃
CH₃
H
H
S
CH₂CH═CH₂

111
2
F
F
F
H
O
CH₃

112
2
F
F
F
H
O
CH₂CH₃

113
2
F
F
F
H
O
CH₂CH₂CH₃

114
2
F
F
F
H
O
CH₂Ph

115
2
F
F
F
H
O
CH₂CH═CH₂

116
2
F
F
F
H
S
CH₃

117
2
F
F
F
H
S
CH₂CH₃

118
2
F
F
F
H
S
CH₂CH₂CH₃

119
2
F
F
F
H
S
CH₂Ph

120
2
F
F
F
H
S
CH₂CH═CH₂

121
2
F
F
F
F
O
CH₃

122
2
F
F
F
F
O
CH₂CH₃

123
2
F
F
F
F
O
CH₂CH₂CH₃

124
2
F
F
F
F
O
CH₂Ph

125
2
F
F
F
F
O
CH₂CH═CH₂

126
2
F
F
F
F
S
CH₃

127
2
F
F
F
F
S
CH₂CH₃

128
2
F
F
F
F
S
CH₂CH₂CH₃

129
2
F
F
F
F
S
CH₂Ph

130
2
F
F
F
F
S
CH₂CH═CH₂

131
2
Cl
Cl
Cl
H
O
CH₃

132
2
Cl
Cl
Cl
H
O
CH₂CH₃

133
2
Cl
Cl
Cl
H
O
CH₂CH₂CH₃

134
2
Cl
Cl
Cl
H
O
CH₂Ph

135
2
Cl
Cl
Cl
H
O
CH₂CH═CH₂

136
2
Cl
Cl
Cl
H
S
CH₃

137
2
Cl
Cl
Cl
H
S
CH₂CH₃

138
2
Cl
Cl
Cl
H
S
CH₂CH₂CH₃

139
2
Cl
Cl
Cl
H
S
CH₂Ph

140
2
Cl
Cl
Cl
H
S
CH₂CH═CH₂

141
2
Cl
Cl
Cl
Cl
O
CH₃

142
2
Cl
Cl
Cl
Cl
O
CH₂CH₃

143
2
Cl
Cl
Cl
Cl
O
CH₂CH₂CH₃

144
2
Cl
Cl
Cl
Cl
O
CH₂Ph

145
2
Cl
Cl
Cl
Cl
O
CH₂CH═CH₂

146
2
Cl
Cl
Cl
Cl
S
CH₃

147
2
Cl
Cl
Cl
Cl
S
CH₂CH₃

148
2
Cl
Cl
Cl
Cl
S
CH₂CH₂CH₃

149
2
Cl
Cl
Cl
Cl
S
CH₂Ph

150
2
Cl
Cl
Cl
Cl
S
CH₂CH═CH₂

151
3
H
H
H
H
O
CH₃

152
3
H
H
H
H
O
CH₂CH₃

153
3
H
H
H
H
O
CH₂CH₂CH₃

154
3
H
H
H
H
O
CH₂Ph

155
3
H
H
H
H
O
CH₂CH═CH₂

156
3
H
H
H
H
S
CH₃

157
3
H
H
H
H
S
CH₂CH₃

158
3
H
H
H
H
S
CH₂CH₂CH₃

159
3
H
H
H
H
S
CH₂Ph

160
3
H
H
H
H
S
CH₂CH═CH₂

161
3
F
F
H
H
O
CH₃

162
3
F
F
H
H
O
CH₂CH₃

163
3
F
F
H
H
O
CH₂CH₂CH₃

164
3
F
F
H
H
O
CH₂Ph

165
3
F
F
H
H
O
CH₂CH═CH₂

166
3
F
F
H
H
S
CH₃

167
3
F
F
H
H
S
CH₂CH₃

168
3
F
F
H
H
S
CH₂CH₂CH₃

169
3
F
F
H
H
S
CH₂Ph

170
3
F
F
H
H
S
CH₂CH═CH₂

171
3
F
Cl
H
H
O
CH₃

172
3
F
Cl
H
H
O
CH₂CH₃

173
3
F
Cl
H
H
O
CH₂CH₂CH₃

174
3
F
Cl
H
H
O
CH₂Ph

175
3
F
Cl
H
H
O
CH₂CH═CH₂

176
3
F
Cl
H
H
S
CH₃

177
3
F
Cl
H
H
S
CH₂CH₃

178
3
F
Cl
H
H
S
CH₂CH₂CH₃

179
3
F
Cl
H
H
S
CH₂Ph

180
3
F
Cl
H
H
S
CH₂CH═CH₂

181
3
F
Br
H
H
O
CH₃

182
3
F
Br
H
H
O
CH₂CH₃

183
3
F
Br
H
H
O
CH₂CH₂CH₃

184
3
F
Br
H
H
O
CH₂Ph

185
3
F
Br
H
H
O
CH₂CH═CH₂

186
3
F
Br
H
H
S
CH₃

187
3
F
Br
H
H
S
CH₂CH₃

188
3
F
Br
H
H
S
CH₂CH₂CH₃

189
3
F
Br
H
H
S
CH₂Ph

190
3
F
Br
H
H
S
CH₂CH═CH₂

191
3
F
CH₃
H
H
O
CH₃

192
3
F
CH₃
H
H
O
CH₂CH₃

193
3
F
CH₃
H
H
O
CH₂CH₂CH₃

194
3
F
CH₃
H
H
O
CH₂Ph

195
3
F
CH₃
H
H
O
CH₂CH═CH₂

196
3
F
CH₃
H
H
S
CH₃

197
3
F
CH₃
H
H
S
CH₂CH₃

198
3
F
CH₃
H
H
S
CH₂CH₂CH₃

199
3
F
CH₃
H
H
S
CH₂Ph

200
3
F
CH₃
H
H
S
CH₂CH═CH₂

201
3
Cl
Cl
H
H
O
CH₃

202
3
Cl
Cl
H
H
O
CH₂CH₃

203
3
Cl
Cl
H
H
O
CH₂CH₂CH₃

204
3
Cl
Cl
H
H
O
CH₂Ph

205
3
Cl
Cl
H
H
O
CH₂CH═CH₂

206
3
Cl
Cl
H
H
S
CH₃

207
3
Cl
Cl
H
H
S
CH₂CH₃

208
3
Cl
Cl
H
H
S
CH₂CH₂CH₃

209
3
Cl
Cl
H
H
S
CH₂Ph

210
3
Cl
Cl
H
H
S
CH₂CH═CH₂

211
3
Cl
Br
H
H
O
CH₃

212
3
Cl
Br
H
H
O
CH₂CH₃

213
3
Cl
Br
H
H
O
CH₂CH₂CH₃

214
3
Cl
Br
H
H
O
CH₂Ph

215
3
Cl
Br
H
H
O
CH₂CH═CH₂

216
3
Cl
Br
H
H
S
CH₃

217
3
Cl
Br
H
H
S
CH₂CH₃

218
3
Cl
Br
H
H
S
CH₂CH₂CH₃

219
3
Cl
Br
H
H
S
CH₂Ph

220
3
Cl
Br
H
H
S
CH₂CH═CH₂

221
3
Cl
CH₃
H
H
O
CH₃

222
3
Cl
CH₃
H
H
O
CH₂CH₃

223
3
Cl
CH₃
H
H
O
CH₂CH₂CH₃

224
3
Cl
CH₃
H
H
O
CH₂Ph

225
3
Cl
CH₃
H
H
O
CH₂CH═CH₂

226
3
Cl
CH₃
H
H
S
CH₃

227
3
Cl
CH₃
H
H
S
CH₂CH₃

228
3
Cl
CH₃
H
H
S
CH₂CH₂CH₃

229
3
Cl
CH₃
H
H
S
CH₂Ph

230
3
Cl
CH₃
H
H
S
CH₂CH═CH₂

231
3
Br
Br
H
H
O
CH₃

232
3
Br
Br
H
H
O
CH₂CH₃

233
3
Br
Br
H
H
O
CH₂CH₂CH₃

234
3
Br
Br
H
H
O
CH₂Ph

235
3
Br
Br
H
H
O
CH₂CH═CH₂

236
3
Br
Br
H
H
S
CH₃

237
3
Br
Br
H
H
S
CH₂CH₃

238
3
Br
Br
H
H
S
CH₂CH₂CH₃

239
3
Br
Br
H
H
S
CH₂Ph

240
3
Br
Br
H
H
S
CH₂CH═CH₂

241
3
Br
CH₃
H
H
O
CH₃

242
3
Br
CH₃
H
H
O
CH₂CH₃

243
3
Br
CH₃
H
H
O
CH₂CH₂CH₃

244
3
Br
CH₃
H
H
O
CH₂Ph

245
3
Br
CH₃
H
H
O
CH₂CH═CH₂

246
3
Br
CH₃
H
H
S
CH₃

247
3
Br
CH₃
H
H
S
CH₂CH₃

248
3
Br
CH₃
H
H
S
CH₂CH₂CH₃

249
3
Br
CH₃
H
H
S
CH₂Ph

250
3
Br
CH₃
H
H
S
CH₂CH═CH₂

251
3
CH₃
CH₃
H
H
O
CH₃

252
3
CH₃
CH₃
H
H
O
CH₂CH₃

253
3
CH₃
CH₃
H
H
O
CH₂CH₂CH₃

254
3
CH₃
CH₃
H
H
O
CH₂Ph

255
3
CH₃
CH₃
H
H
O
CH₂CH═CH₂

256
3
CH₃
CH₃
H
H
S
CH₃

257
3
CH₃
CH₃
H
H
S
CH₂CH₃

258
3
CH₃
CH₃
H
H
S
CH₂CH₂CH₃

259
3
CH₃
CH₃
H
H
S
CH₂Ph

260
3
CH₃
CH₃
H
H
S
CH₂CH═CH₂

261
3
F
F
F
H
O
CH₃

262
3
F
F
F
H
O
CH₂CH₃

263
3
F
F
F
H
O
CH₂CH₂CH₃

264
3
F
F
F
H
O
CH₂Ph

265
3
F
F
F
H
O
CH₂CH═CH₂

266
3
F
F
F
H
S
CH₃

267
3
F
F
F
H
S
CH₂CH₃

268
3
F
F
F
H
S
CH₂CH₂CH₃

269
3
F
F
F
H
S
CH₂Ph

270
3
F
F
F
H
S
CH₂CH═CH₂

271
3
F
F
F
F
O
CH₃

272
3
F
F
F
F
O
CH₂CH₃

273
3
F
F
F
F
O
CH₂CH₂CH₃

274
3
F
F
F
F
O
CH₂Ph

275
3
F
F
F
F
O
CH₂CH═CH₂

276
3
F
F
F
F
S
CH₃

277
3
F
F
F
F
S
CH₂CH₃

278
3
F
F
F
F
S
CH₂CH₂CH₃

279
3
F
F
F
F
S
CH₂Ph

280
3
F
F
F
F
S
CH₂CH═CH₂

281
3
Cl
Cl
Cl
H
O
CH₃

282
3
Cl
Cl
Cl
H
O
CH₂CH₃

283
3
Cl
Cl
Cl
H
O
CH₂CH₂CH₃

284
3
Cl
Cl
Cl
H
O
CH₂Ph

285
3
Cl
Cl
Cl
H
O
CH₂CH═CH₂

286
3
Cl
Cl
Cl
H
S
CH₃

287
3
Cl
Cl
Cl
H
S
CH₂CH₃

288
3
Cl
Cl
Cl
H
S
CH₂CH₂CH₃

289
3
Cl
Cl
Cl
H
S
CH₂Ph

290
3
Cl
Cl
Cl
H
S
CH₂CH═CH₂

291
3
Cl
Cl
Cl
Cl
O
CH₃

292
3
Cl
Cl
Cl
Cl
O
CH₂CH₃

293
3
Cl
Cl
Cl
Cl
O
CH₂CH₂CH₃

294
3
Cl
Cl
Cl
Cl
O
CH₂Ph

295
3
Cl
Cl
Cl
Cl
O
CH₂CH═CH₂

296
3
Cl
Cl
Cl
Cl
S
CH₃

297
3
Cl
Cl
Cl
Cl
S
CH₂CH₃

298
3
Cl
Cl
Cl
Cl
S
CH₂CH₂CH₃

299
3
Cl
Cl
Cl
Cl
S
CH₂Ph

300
3
Cl
Cl
Cl
Cl
S
CH₂CH═CH₂

EXAMPLE 1

Hereinafter, the present invention will be further described in more detail with reference to Example, which the present invention is not limited to.

EXAMPLE 1

A mixture of 1.15 g of 3-bromopropanol, 7.5 g of toluene and 0.12 g of tetra-n-butylammonium bromide was heated to 60° C., and thereto was added a slurry solution of 1.5 g of 4-(benzyloxy)phenol, 7.5 g of water and 1.22 g of a 27% aqueous sodium hydroxide solution with stirring. After addition, the mixture was stirred at 60° C. for 17 hours. In this period, 0.40 g of 3-bromopropanol and 0.40 g of a 27% aqueous sodium hydroxide solution were further added thereto at the time point of 13 hours. Subsequently, the reaction mixture was cooled to 20° C. After 3.0 g of a 20% aqueous sulfuric acid solution and 15.0 g of toluene were added thereto, the mixture was stirred and then separated. The obtained organic layer was washed with 7.5 g of a 1% aqueous sodium hydroxide solution once and with 7.5 g of water once, and concentrated under reduced pressure to give 2.0 g of 3-(4-benzyloxy)phenoxy)-1-propyl alcohol (purity: 93%, yield: 94%).

INDUSTRIAL APPLICABILITY

According to the process of the present invention, the alcohol compound represented by the formula (3) can be produced efficiently with reduced environmental burdens.

Claims

1. A process for production of an alcohol compound represented by the formula (3):
2. The process for production of an alcohol compound according to claim 1, wherein Z is an oxygen atom.
3. The process for production of an alcohol compound according to claim 1 or 2, wherein R is a benzyl group.
4. The process for production of an alcohol compound according to claim 1, wherein the water-immiscible organic solvent is a hydrocarbon compound or a chain ether compound.
5. The process for production of an alcohol compound according to claim 1, wherein the water-immiscible organic solvent is toluene.
6. The process for production of an alcohol compound according to claim 1, wherein a reaction temperature is 50° C. to 100° C.
7. The process for production of an alcohol compound according to claim 1, wherein the phase-transfer catalyst is a tetra-n-butylammonium salt.
8. The process for production of an alcohol compound according to claim 1, wherein the phenol represented by the formula (1) is 2,6-dichloro-4 -(benzyloxy)phenol.
9. The process for production of an alcohol compound according to claim 1, wherein n is 3.
10. The process for production of an alcohol compound according to claim 1, wherein the haloalcohol represented by the formula (2) is 3-bromo-1-propanol.
11. The process for production of an alcohol compound according to claim 2, wherein the water-immiscible organic solvent is a hydrocarbon compound or a chain ether compound.
12. The process for production of an alcohol compound according to claim 3, wherein the water-immiscible organic solvent is a hydrocarbon compound or a chain ether compound.
13. The process for production of an alcohol compound according to claim 2, wherein the water-immiscible organic solvent is toluene.
14. The process for production of an alcohol compound according to claim 2, wherein a reaction temperature is 50° C. to 100° C.
15. The process for production of an alcohol compound according to claim 2, wherein the phase-transfer catalyst is a tetra-n-butylammonium salt.
16. The process for production of an alcohol compound according to claim 2, wherein the phenol represented by the formula (1) is 2,6-dichloro-4-(benzyloxy)phenol.
17. The process for production of an alcohol compound according to claim 2, wherein n is 3.
18. The process for production of an alcohol compound according to claim 2, wherein the haloalcohol represented by the formula (2) is 3-bromo-1-propanol.

Priority Claims (1)

Number	Date	Country	Kind
2006-184254	Jul 2006	JP	national

PCT Information

Filing Document	Filing Date	Country	Kind	371c Date
PCT/JP2007/063289	7/3/2007	WO	00	12/31/2008

Publishing Document	Publishing Date	Country	Kind
WO2008/004544	1/10/2008	WO	A

US Referenced Citations (1)

Number	Name	Date	Kind
5922880	Sakamoto et al.	Jul 1999	A

Foreign Referenced Citations (6)

Number	Date	Country
1 221 411	Jul 2002	EP
9-151172	Jun 1994	JP
9-504014	Apr 1997	JP
2005-325026	Nov 2005	JP
WO 9511240	Apr 1995	WO
WO 2004099145	Nov 2004	WO

Related Publications (1)

	Number	Date	Country
	20090259074 A1	Oct 2009	US

Process for production of alcohol compound

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