Tetrahydrofuran → 5-(Hydroxymethyl)-2-methoxybenzonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 3-cyano-4-methoxybenzoate (5g), tetrahydrofuran (25 mL) and sodium borohydride (1.98 g) was heated at 45° C. The mixture was dropwise added with methanol (6.36 mL) at 45-55° C. over 15 minutes and then refluxed for 3.5 hours. After cooling to 0° C., the mixture was added with an aqueous saturated ammonium chloride solution at the same temperature. The mixture was stirred at room temperature for an hour, and extracted with ethyl acetate. The organic layer was washed successively with water, an aqueous saturated sodium bicarbonate solution and brine. The organic layer was dried over magnesium sulfate and evaporated in vacuo. The residual solid was triturated with diisopropyl ether to give 3-cyano-4-methoxybenzyl alcohol (3.75 g) as a pale brown solid.

Provenance & Evidence