Methanol → 3-Ethylaminophenol

Participants

Reaction Steps

To a solution of 161 g of 3-acetamidophenol in 800 ml of tetrahydrofuran was added dropwise over 1-2 hr 275 ml of a 1.0M solution of borane-methyl sulfide in dichloromethane. The reaction was heated to reflux 4-5 hr and then poured slowly into 1 l of methanol. The solvent was evaporated to a heavy syrup which deposited crystals on cooling and scratching. The solid was collected by filtration and redisolved in methanol. Evaporation and crystallization as above gave a 74% yield of 3-(ethylamino) phenol.

Provenance & Evidence