Preparing 2-arylalkanoic acid derivatives

Details Preparing 2-arylalkanoic acid derivatives Preparing 2-arylalkanoic acid derivatives

1977-05-02

1980-02-19

Myers, Jane S.

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

Organic compounds

Carboxylic acid esters

2603433R, 560 51, 560 53, 560126, 560176, 562462, 562463, 562496, 562508, 562578, C07C 6352, C07C 6976

Patent

active

041895967

ABSTRACT:
2-Aryl-C.sub.2 to C.sub.5 -alkanoic acids and esters thereof are prepared by heating a 2-(2-oxo-3-cyclohexenyl)-alkanoic acid or ester derivative in the presence of a sulfonic acid or a phosphonic acid at 75.degree. C. to 130.degree. C. while providing a means for removing water from the reaction mixture. In the process new butenolide derivative intermediates have been discovered. Alternatively, the 2-aryl-C.sub.2 to C.sub.6 -alkanoic acids can be prepared from the butenolides by forming a mixture of the 2-(2-oxo-3-cyclohexenyl)-alkanoic acid with acetic anhydride in the presence of an acid scavenging base, allowing the mixture to stand for a time sufficient to form an acetate intermediate, heating the resulting mixture to about 75.degree. C. to about 130.degree. C. to form the betenolide intermediates. Thereafter these intermediates can be heated with sulfonic or phosphonic acid as above while removing water to form the 2-aryl-C.sub.2 to C.sub.6 -alkanoic acid or adding a carboxylic acyl halide and water to form acetic acid and mineral acid in the mixture, and this resulting mixture can be heated to 75.degree. C. to 130.degree. C. for a time sufficient to form 2-aryl-C.sub.2 to C.sub.6 -alkanoic acid products which have a variety of uses.

REFERENCES:
patent: 3256300 (1966-06-01), Wygant et al.
patent: 3758513 (1973-09-01), Heelsa
patent: 3850952 (1974-11-01), Kuo et al.
patent: 4008270 (1977-02-01), White
patent: 4096177 (1978-06-01), Baiocchi
Palazzo et al., Tetrahedron Letters, No. 46, pp. 4739-4742 (1968).

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