2-Amino-6-chlorobenzoic acid → (2-Amino-6-chlorophenyl)methanol

Participants

Reaction Steps

To a suspension of lithium aluminum hydride (1.1 g, 29.1 mmol) in tetrahydrofuran (150 mL) was added 2-amino-6-chlorobenzoic acid (5 g, 29.1 mmol) at 0° C. The mixture was stirred at room temperature for 16 h. Then, the reaction mixture was quenched with sodium sulfate decahydrate (3 g) and brine (10 ml) and filtrated through a pad of Celite. The organic layer was concentrated in vacuo and the residue was chromatographed on a column of silica gel eluting with ethyl acetate/hexane (1:2) to give 2.4 g (52%) of the title compound as a colorless oil.

Provenance & Evidence