JPS6413062A - Production of anilinoalkanecarboxylic acids - Google Patents

Abstract

PURPOSE:To industrially and advantageously obtain the titled compounds useful as an intermediate for insecticides in high purity, by condensing inexpensive p-chlorobenzotrifluoride with D-valines in the presence of a catalyst in a polar solvent and then carrying out nuclear chlorination. CONSTITUTION:P-chlorobenzotrifluoride expressed by formula I is subjected to condensation reaction with a compound expressed by formula II (R is lower alkyl; M is H, Na, or K; asymmetric carbon atom indicates R, S or RS structure), such as K salt of D-valine, in an aprotic polar solvent, such as N- methylpyrrolidone, in the presence of a catalyst, such as salt of Cu or Ni, e.g. CuCl2 in an amount of 0.5-30mol% based on the compound expressed by formula I, preferably at 100-180 deg.C for 1-15hr to form a compound expressed by formula III, which is then subjected to nuclear chlorination with a nuclear chlorinating agent, such as N-chlorosuccinimide, in a solvent, such as CCl4, preferably at 0-100 deg.C to afford the aimed compounds, expressed by formula IV and useful as an intermediate for synthetic pyrethroid insecticides.