Water → (1-Methylcyclohexyl)methanol

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of LiAlH4 (20 mmol) in anhydrous THF (10 mL) at 4° C. was added 1-methyl-cyclohexanecarboxylic acid (i, 7.0 mmol) in 50 mL of THF dropwise over a period of 1 hour. The solution was stirred at refluxing temperature under N2 for 6 hours. The solution was cooled to 4° C. by ice bath, and 1 mL of 1 N NaOH (1 mL) followed by H2O (2 mL) was slowly added to the solution to quench the reaction. The solution was stirred at 23° C. for 1 hour and then filtered to remove solid material. The solution was concentrated. Purification by flash silica gel chromatography (ethyl acetate/hexanes, 1:2) gave the product, (1-methyl-cyclohexyl)-methanol (ii), in 82% yield.

Provenance & Evidence