Hydrochloric Acid → (3-Methoxy-1,2-phenylene)dimethanol

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-methoxy-1-(3H)-isobenzofuranone (described in J. Org. Chem., 52, 129 (1987); 1.64 g, 10.0 mmol) in tetrahydrofuran (30 ml) was added lithium borohydride (652.2 mg, 30 mmol) with stirring at 0° C., and the mixture was heated under reflux for 2.5 hours with stirring. After cooling the mixture to room temperature, a 2N aqueous solution of hydrochloric acid (20 ml) was added thereto. The product was extracted with ethyl acetate, and the organic layer was washed with a saturated aqueous solution of sodium chloride. The filtrate was concentrated under reduced pressure to give a solid residue. The residue was subjected to chromatography on a silica gel (30 g) column (eluent; ethyl acetate:hexane=2:1˜4:1) to afford the title compound (1.31 g, 78% yield) as a colorless solid (mp. 95° C.).

Provenance & Evidence