2'-Aminoacetophenone → 2-Amino-alpha-methylbenzenemethanol

Participants

Reaction Steps

Sodium borohydride (40 g, 1.0 mol) was added portionwise to a stirred solution of o-aminoacetophenone (80 g) in methanol (800 ml) at 0°, allowing the effervescence to subside between each addition. Cooling was removed and the mixture allowed to warm to reflux temperature to complete the reaction. When cool, the solvent was evaporated and the residue partioned between dichloromethane-water. The organic solution was washed successively with water and brine, dried (anhyd. MgSO4), filtered and evaporated to a light yellow oil which crystallised from petroleum spirit (40°-60°) to give white crystals (52 g, 64%), m.p. 50°-52°.

Provenance & Evidence