Methyl Acrylate → 3-(4-Amino-3,5-dimethylphenyl)propan-1-ol

Participants

Reaction Conditions

Reaction Steps

Palladium acetate (68 mg) and 720 mg of tris-o-tolylphosphine were mixed in a Schlenk tube under a nitrogen atmosphere. After 15 ml of triethylamine, 6 g of 4-bromo-2,6-dimethylaniline and 3.2 g of methyl acrylate had been added, the tube was heated to 100° C. in an oil bath and kept there for 6 h. The mixture was added to water and extracted 3 times with ethyl ether. After drying in vacuum 6.2 g of a yellow solid was obtained. The solid was dissolved in THF and 3.5 g of lithium aluminum hydride was added. After 6 h the reaction was poured into water and purified by column chromatography (silica, hexane:ethyl acetate 2:1). A mixture of 3-(4-amino-3,5-dimethyl-phenyl-propan-1-ol and 3-(4-amino-3,5-dimethylphenyl)propan-1-ol (3.5 g) was obtained. The mixture was dissolved in ethyl acetate and 50 mg of palladium (10 wt %) on carbon was added. Hydrogen was bubbled through the solution for one h. After removing the palladium catalyst and the solvent, 3.1 g of 3-(4-amino-3,5-dimethyl-phenyl)-prop-2-en-1-ol was obtained. 1H-NMR (200 MHz, CDCl3): 6.77 (s, 2H), 3.64 (t, 2H), 3.47 (b s, 2H) 2.54 (t, 2H), 2.15 (s, 6H), 1.82 ppm (m, 2H).

Provenance & Evidence