Preparation of .alpha.-arylalkanoic acids

Details Preparation of .alpha.-arylalkanoic acids Preparation of .alpha.-arylalkanoic acids

1988-05-06

1990-03-27

Shippen, Michael L.

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

Organic compounds

Carboxylic acids and salts thereof

562466, C07C 5116

Patent

active

049122541

ABSTRACT:
Pharmaceutically useful optically active .alpha.-arylalkanoic acids or esters, ortho esters, or amides thereof are stereoselectively prepared by contacting an aryl magnesium Grignard reagent with an optically active .alpha.-substituted acyl halide to form the optically active aryl .alpha.-substituted alkyl ketone, which is ketalized and rearranged to the desired optically active .alpha.-arylalkanoic acid or the corresponding ester, ortho ester or amide. In an alternate embodiment, the aryl .alpha.-substituted alkyl ketone is reduced to the corresponding alkanol, which is rearranged to the .alpha.-arylalkanal. The alkanal so produced is converted to the desired optically active .alpha.-arylalkanoic acid by conventional methods.

REFERENCES:
Seebach, Angew. Chem. Internat. Ed., pp. 619-621, (1968).
Smissman, J. Org. Chem., pp. 4005-4007, (1965).
Tsuchihashi, Tetrahedron Letters, 22(43), pp. 4305-4308.

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