Process for preparing phenethanol ethers by the reduction of cor

Details Process for preparing phenethanol ethers by the reduction of cor Process for preparing phenethanol ethers by the reduction of cor

1991-09-06

1992-06-23

Cintins, Marianne M.

Organic compounds -- part of the class 532-570 series

Organic compounds

Oxygen containing

562478, C07C 4128

Patent

active

051244896

ABSTRACT:
Substituted phenethanol ethers are prepared by the catalytic reduction of corresponding substituted phenylglyoxal acetals. The catalytic reduction is carried out by reacting a substituted phenylglyoxal acetal with hydrogen in the presence of an acid catalyst and a metal catalyst. Certain substituted phenylglyoxal acetals, and more particularly, 4-hydroxyphenylglyoxal dialkyl acetals are prepared by reacting 4-hydroxyacetophenone with a primary or a secondary alkyl alcohol in the presence of a hydrogen ion (H+) source and a nitrosonium ion (NO+) source.

REFERENCES:
March, Jerry; "Advanced Organic Chemistry" (1985) John Wiley & Sons New York, pp. 393-394 (3rd Ed.).
Larock, Richard; "Comprehensive Organic Transformations" (1989) pp. 35-36.
Sandler, Stanley et al.; "Organic Functional Group Preparations" (1972) Academic Press, New York (vol. III) p. 68.
Noller, Carl "Chemistry of Organic Compounds" (1965) W. B. Saunder Co. Philadelphia, p. 243 and 844.
2 Pharmaceutical Manufacturing Encyclopedia, 1009-1010 (2nd ed. 1988).
Hallberg, et al., a New Route to 4-(2'-Methoxyethyl)Phenol via Palladium-catalyzed Arylation of Methyl Vinyl Ether, 15(13) Synthetic Com., 1131-6 (1985).
Baird et al., Neighboring Carbon and Hydrogen, L. I. Dienones from AR, .THETA.-3 Participation. Isolation and Behavior of Spiro(2,5)octa-1,4-diene-3-one, 85 Am. Chem. Soc. 567-575 (1962).
Communication to the Editor from Baird et al, 79 Am. Chem. Soc. 756-757 (1957).

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