Sodium Hydroxide → Permethric acid

Participants

Reaction Steps

Conversion to high cis 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylic acid (compound C acid). Sodium hydroxide (20 g, 0.5 mole) in 100 ml of water was added to the reaction mixture above with vigorous stirring and the whole was heated at 100° for 5 hours under conditions allowing for the distillation of the tert-butanol present from the Phase (a) reaction. The mixture was allowed to cool to room temperature, then washed with ether and made acidic with concentrated hydrochloric acid. The acidified mixture was extracted with ether and the ether extracts were combined, washed with brine, dried over magnesium sulfate and concentrated to give, after distillation, 18.22 g (87% yield) of 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylic acid, bp 102°-105°/0.3 mm Hg, purity 97.3%, C/T=78/22.

Provenance & Evidence