Cyclohexanone → 1-(2-Nitrophenyl)cyclohexan-1-ol

Participants

Reaction Steps

40.16 mL (80.32 mmol) of phenylmagnesium chloride (2 M in THF) is added dropwise at −50° C. to a solution of 20.0 g (80.32 mmol) of 2-nitroiodobenzene in absolute THF (150 mL) under a nitrogen atmosphere. After stirring for 15 minutes, 9.98 mL (96.30 mmol) of cyclohexanone is added quickly. The mixture is heated to RT and stirred for a further 2 hours. Saturated aqueous ammonium chloride solution is added and the aqueous phase is exhaustively extracted with EtOAc. The combined organic extracts are washed with saturated aqueous NaCl solution, dried with sodium sulfate, and evaporated down in vacuo. After column chromatography (silica gel, hexane/EtOAc 20:1), the product is obtained as a brownish oil. Yield: 5.20 g (29%); Rf=0.26 (silica gel, hexane/EtOAc 10:1); ESI-MS: [M+H−H2O]+=204.

Provenance & Evidence