Water → (3-Tert-butylphenyl)methanol

Participants

Reaction Steps

To a suspension (40 ml) of lithium aluminum hydride (1.38 g, 36.2 mmol) in ether was added dropwise a solution of 3-tert-butylbenzoic acid (3.13 g, 17.6 mmol) in ether (40 ml) under ice-cooling, and the mixture was stirred at room temperature for 2 hrs. After completion of the reaction, water (1.38 ml), 15% aqueous sodium hydroxide solution (1.38 ml) and water (4.2 ml) were successively added dropwise slowly under ice-cooling. The obtained solid was filtered with celite, and washed with ethyl acetate. The filtrate was concentrated, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1, 4:1) to give 3-tert-butylbenzyl alcohol (2.59 g, 90%) as a colorless transparent oil.

Provenance & Evidence