Benzyl Alcohol → tert-Butyl-3-aminobenzoate

Participants

Reaction Steps

A mixture of 3-nitrophenylacetic acid (5 g), benzyl alcohol (2.9 ml) and 4,4-dimethylaminopyridine (300 mg) in dry dichloromethane (50 ml) was treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (7.4 g). The resulting yellow mixture was stirred at 23° for 3 days whereupon the solvent was removed in vacuo. The residue was partitioned between water (100 ml) and ethyl actate (100 ml) and the organic phase washed with water (2×100 ml) and saturated brine (100 ml) then dried and evaporated. The residue was chromatographed with hexane-EA (4:1) as eluent then again with isohexane-DCM (1:1) as eluent to give the title compound (2.05 g) as a pale yellow oil.

Provenance & Evidence