Chloroacetyl chloride → (-)-(1R,2S)-2-phenylcyclohexyl chloroacetate

Participants

Reaction Steps

A mixture of 790 g (4.48 mole) of pure (-)-(1R,2S)-2-phenylcyclohexanol, 1.5 L of methylene chloride, 450 mL (5.625 mole) of chloroacetyl chloride, and 2.2 g (0.96 mole) of 4-dimethylaminopyridine was heated at reflux for 8 hours. On cooling, the reaction mixture was stirred with 2 ×1.5 L=3.0 L of saturated NaHCO3 for 30 minutes. The organic layer was dried (Na2SO4) and evaporated to dryness, finally at 0.5 mm for 4 hours to afford 1.136 kg of the title compound (100%) as an oil.

Provenance & Evidence