Ammonia → 1-(3,5-Dimethylphenyl)ethanamine

Participants

Reaction Steps

3,5-Dimethylacetophenone (3.0 g, 20.2 mmol) was dissolved in ethanolic NH3 solution (2 M in ethanol, 50 ml), tetrapropylorthotitanate (11 ml, 40.4 ml) was added and the mixture was stirred for 6 h at room temperature. NaBH4 (1.16 g, 30.4 mmol) was then added carefully to the reaction solution and the mixture was stirred overnight at room temperature. The reaction mixture was poured into aqueous ammonia solution and filtered. The solid was washed twice more with ethyl acetate (50 ml). The phases were separated and the aqueous phase was extracted twice more with ethyl acetate. The combined organic phases were washed with HCl solution (2 N, 60 ml), the aqueous phase was adjusted to pH 11 with NaOH solution and extracted three times with ethyl acetate (100 ml). The organic phase was washed with saturated NaCl solution (100 ml), dried over MgSO4 and concentrated to small volume. The resulting crude product was used without further purification. Yield: 43%.

Provenance & Evidence