Water → Cyclohexanecarboxylic acid, 4-(hydroxymethyl)-, methyl ester

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Reaction Steps

To a slurry of NaH (440 mg, 11 mmol) in THF (22 mL) is added trans-1,4-cyclohexanedimethanol (1.44 g, 10 mmol) at 0° C., and the mixture is stirred for 1 h while warming to room temperature. Benzyl bromide (1.2 mL, 10 mmol) is added dropwise followed by tetrabutylammonium iodide (185 mg, 0.5 mmol). The reaction is heated to 60° C. for 15 hours. After cooling to room temperature, H2O is added and the aqueous layer is extracted with EtOAc. The combined organic layer (dried with MgSO4) is concentrated. The desired product, (4-benzyloxymethyl-cyclohexyl)-methanol, is obtained (1.40 g, 60%) after purification using silica gel column chromatography (eluent: EtOAc/hexane).

Provenance & Evidence