Water → 2,2-Dimethyl-3-phenylcyclopropanecarbonitrile

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Reaction Steps

To a solution of 1-cyano-2,2-dimethyl-3-phenyl-cyclopropanecarboxylic acid (13.6 g, 63 mmol) in DMSO (125 mL) was added LiCl (10.72 g, 252 mmol) followed by NaHCO3 (7.96 g, 94.5 mmol) and water (4.55 g, 252 mmol). Gas evolution was observed, and within 30 minutes enough solids were dissolved to allow the milky mixture to stir. The reaction mixture was stirred at 170° C. for 18 hours, then cooled and poured into a mixture of water and brine (7/1, 800 mL) and extracted with ethyl ether. The combined organic extracts were dried over Na2SO4, filtered and evaporated under reduced pressure to give 7.79 g (76% yield) of 2,2-dimethyl-3-phenyl-cyclopropanecarbonitrile (3/1, cis/trans mixture).

Provenance & Evidence