Process for preparing aryl- or heteroarylhexadienoic acids

Details Process for preparing aryl- or heteroarylhexadienoic acids Process for preparing aryl- or heteroarylhexadienoic acids

1980-12-02

1982-10-19

Rotman, Alan L.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546301, 546318, 546326, 549 66, 549 71, 549 79, 549471, 562471, 562495, 562496, C07D21355, C07D33324, C07C 5742, C07C 51347

Patent

active

043551688

ABSTRACT:
There is disclosed and claimed a process for preparing aryl- and heteroarylhexadienoic acids which is characterized in that an aryl- or heteroarylacetylene having the formula: R--C.tbd.CH, wherein R is an aryl or heteroaryl group, optionally substituted and having in the aggregate up to 20 carbon atoms, is reacted with 3-butenoic acid CH.sub.2 .dbd.CH--CH.sub.2 --COOH, in an alcoholic medium, at temperatures maintained between 50.degree. C. and 120.degree. C., approximately, in the presence of a catalyst selected from among the phosphinic complexes of rhodium having the formulas: III, Rh(PR'.sub.3).sub.n L.sub.m X associated with alkaline salts of carboxylic acids having up to 4 carbon atoms, and IV, Rh(PR'.sub.3).sub.n L.sub.p.sup.+ Y.sup.-, wherein R' is a hydrocarbyl group having up to 12 carbon atoms; "L" is a linear or cyclic olefin selected from among the olefins having from 2 to 10 carbon atoms and the chelating olefins having from 6 to 8 carbon atoms, n is an integer from 1 to 3, m is an integer from 0 to 2 and such that n+m=2 or 3, and p is an integer from 0 to 3 and such that n+p=3 or 4; X is an anion selected from among the haloid anions, preferably the hydrochloric anion, and the anions of carboxylic acids having up to 4 carbon atoms and Y is a sparingly coordinating anion, preferably selected from PF.sub.6.sup.- and BF.sub.4.sup.-.
The compounds obtained are used as intermediates for organic syntheses, with particular regard to the so-called "fine chemicals" such as, for example, additives for polymers and paints, plasticizers, and the like.

REFERENCES:
patent: 4011339 (1977-03-01), Galantay et al.
patent: 4219659 (1980-08-01), Fujisawa et al.
patent: 4221915 (1980-09-01), Kondo et al.

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