Hydrochloric Acid → HCID 69104144, compound

Participants

Reaction Steps

To a suspension of lithium aluminum hydride (2.54 g) in tetrahydrofuran (50 ml) was added dropwise a solution of 4-bromo-2-(cyclohexyloxy)benzoic acid (10 g) in tetrahydrofuran (50 ml) at 5° C. under nitrogen, and the mixture was stirred at room temperature for 2.5 hours. The resulting mixture was poured into 1N hydrochloric acid and the aqueous layer was extracted with ethyl acetate. The organic layer was washed successively with 1N hydrochloric acid, aqueous-sodium bicarbonate and brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=10:1 to 5:1) to give (4-bromo-2-cyclohexyloxyphenyl)methanol (5.47 g).

Provenance & Evidence