Claims
- 1. A process for the preparation of (S) .alpha.-cyano-3-phenoxy-benzyl alcohol comprising reacting in the presence of an acid agent (R,S) .alpha.-cyano-3-phenoxy-benzyl alcohol and the lactone of cis 2,2-dimethyl-3S-(dihydroxymethyl)-cyclopropane-1R-carboxylic acid to obtain a mixture of (1R,5S) 6,6-dimethyl-4(R)-[(S)-cyano-(3'-phenoxyphenyl)-methoxy]-3-oxa-bicyclo-(3,1,0)-hexan-2-one and (1R,5S) 6,6-dimethyl-4(R)-[(R)-cyano-(3'-phenoxyphenyl)-methoxy]-3-oxa-bicyclo-(3,1,0)-hexan-2-one, separating the two isomers by physical means and hydrolyzing (1R,5S) 6,6-dimethyl-4(R)-[(S)-cyano-(3'-phenoxy-phenyl)-methoxy]-3-oxa-bicyclo-(3,1,0)-hexan-2-one in an acid media to obtain (S) .alpha.-cyano-3-phenoxy-benzyl alcohol.
- 2. The process of claim 1 wherein the acid agent present in the reaction of the racemic alcohol and the lactone is preferably selected from the group consisting of p-toluene sulfonic acid, methane sulfonic acid, perchloric acid, m-nitrobenzene sulfonic acid, 5-sulfosalicylic acid and camphosulfonic acid.
- 3. The process of claim 1 wherein the physical separation is effected by chromatography over silica gel.
- 4. The process of claim 1 wherein the hydrolysis is effected with p-toluene sulfonic acid.
Priority Claims (1)
Number |
Date |
Country |
Kind |
78 02621 |
Jan 1978 |
FRX |
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PRIOR APPLICATION
This application is a divisional of copending, commonly assigned U.S. patent application Ser. No. 973,791 filed Dec. 28, 1978, now U.S. Pat. No. 4,273,727.
US Referenced Citations (1)
Number |
Name |
Date |
Kind |
4024163 |
Elliott et al. |
May 1977 |
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Non-Patent Literature Citations (2)
Entry |
Ruzo et al., J. Agric. Food Chem., vol. 25, pp. 1385-1394, (1977). |
Ruzo et al., Tetrahedron Letters, No. 35, pp. 3045-3048, (1976). |
Divisions (1)
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Number |
Date |
Country |
Parent |
973791 |
Dec 1978 |
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