Claims
- 1. 1-(4-tert.-Alkoxy-phenyl)-butan-3-one and -but-1-en-3-one derivatives of the general formula III ##STR6## where R is H or CH.sub.3 and the broken line may or may not be an additional bond between the carbon atoms which it links.
- 2. A process for the preparation of 1-(4-hydroxyphenyl)-butan-3-one, comprising:
- (a) preparing a compound of the formula: ##STR7## wherein R is H or CH.sub.3 by condensing acetone under alkaline conditions with a compound of the formula: ##STR8## (b) hydrogenating compound IIIa after or while it is formed thereby yielding a compound of the formula: ##STR9## (c) eliminating isobutene or 2-methyl-but-1(2)-ene from compound IIIb at a temperature of 40.degree. to 150.degree. C. in the presence of an acid.
- 3. The process of claim 2, wherein the molar ratio of acetone to benzaldehyde reactant ranges from 1-10:1.
- 4. The process of claim 2, wherein said condensation reaction between said benzaldehyde compound and acetone is conducted in the presence of a catalyst selected from the group consisting of alkali metal hydroxides, alkaline earth metal hydroxides, alkali metal alcoholates, and alkaline earth metal alcoholates.
- 5. The process of claim 4, wherein said catalyst is present in an amount of 0.0001-0.1 mole per mole of aldehyde reactant.
- 6. The process of claim 2, wherein said condensation reaction is conducted at a temperature of from 0.degree. to 50.degree. C.
- 7. The process of claim 2, wherein said hydrogenation step is conducted over a palladium or platinum catalyst supported on active charcoal, silica gel or aluminum oxide.
- 8. The process of claim 2, wherein said acid is selected from a group consisting of aqueous sulfuric acid, aqueous phosphoric acid, aqueous hydrochloric acid, aqueous formic acid and aqueous acetic acid.
- 9. The process of claim 8, wherein the amount of acid present ranges from 0.001 to 0.5 moles per mole of compound IIIb.
- 10. The process of claim 2, wherein in step (b) of said process, said compound IIIa is hydrogenated after it is formed.
Priority Claims (1)
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3015359 |
Apr 1980 |
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Parent Case Info
This application is a continuation of application Ser. No. 250,935, filed Apr. 6, 1981.
US Referenced Citations (8)
Foreign Referenced Citations (4)
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702894 |
Feb 1941 |
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1098951 |
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DEX |
2145308 |
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DEX |
1094417 |
Jul 1966 |
GBX |
Non-Patent Literature Citations (3)
Entry |
mcOmie, "Protective Groups in Organic Chem.", pp. 157-167 (1973), Blenun Press. |
Papa et al., I.A.C.S., Vol. 70, pp. 3358-3360 (1948). |
House, Modern Synthetic Reactions, pp. 632-642 (1972). |
Continuations (1)
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250935 |
Apr 1981 |
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