Synthesis of fatty acids using organocopper (I) ate complexes derived from Grignard reagents. Academic Article uri icon

abstract

  • Fatty acid esters have been synthesized in good yield by reaction between copper(I) ate complexes formed from methylcopper(I) and primary or secondary Grignard reagents and esters of primary iodoalkylcarboxylic acids. The synthetic method is illustrated with procedures for CH 2 =CH(CH 2 ) 19 CO 2 C 2 H 5 , C 6 H 5 CH 2 O(CH 2 ) 16 CO 2 C 2 H 5 , CH 3 (CH 2 ) 25 CO 2 C 2 H 5 , CH 3 O 2 C(CH 2 ) 22 CO 2 CH 3 , C 2 H 5 O 2 C(CH 2 ) 32 CO 2 C 2 H 5 , and CH 3 (CH 2 ) 4 CH(CH 3 )(CH 2 ) 10 CO 2 CH 3 . The reaction sequence uses starting Grignard reagent with high efficiency, provides product mixtures that are conveniently worked up, and tolerates a variety of functional groups. It provides the most direct route presently available to a variety of representative classes of simple fatty acids. 1975, American Chemical Society. All rights reserved.

published proceedings

  • J Org Chem

altmetric score

  • 3

author list (cited authors)

  • Bergbreiter, D. E., & Whitesides, G. M.

citation count

  • 41

complete list of authors

  • Bergbreiter, DE||Whitesides, GM

publication date

  • March 1975