Water → (1S,3S)-2,2-dimethyl-3-phenylcyclopropane-1-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of 2,2-dimethyl-3-phenyl-cyclopropanecarbonitrile (cis/trans mixture, 3.2 g, 18.7 mmol) and freshly ground KOH (3.143 g, 56.1 mmol) in ethylene glycol was heated at 165° C. for 28 hours. The reaction mixture was then cooled and poured into a mixture of water and brine (300 mL). The resulting mixture was extracted 3 times with ethyl ether, the combined organic extracts were dried over Na2SO4, filtered and evaporated under reduced pressure to give 3.36 g (95% yield) of trans-2,2-dimethyl-3-phenyl-cyclopropanecarboxylic acid.

Provenance & Evidence