Toluene → HCID 53822285, compound

Participants

Reaction Conditions

Reaction Steps

18 ml (0.23 mole) of dimethylformamide are added dropwise in the course of a few minutes, whilst stirring, to 120 g (0.90 mole) of anhydrous aluminum chloride, resulting in a strongly exothermic reaction. 8.2 g (89.0 millimoles) of toluene are then added dropwise at 60°-70° C. Thereafter, 10.0 g (89.2 millimoles) of 1,2-cyclopropanedicarboxylic acid anhydride are added, a little at a time, at the same temperature, and the mixture is stirred for a further hour at 70° C. The melt is then introduced into 1 kg of ice. The solid which has precipitated is filtered off, washed with water and dried under reduced pressure at 50° C. 16.3 g (90% of theory) of cis-2-(p-toluoyl)-cyclopropanecarboxylic acid are obtained as colorless crystals, of melting point 165°-166° C. after recrystallization from ethyl acetate.

Provenance & Evidence