Triethylamine → 4-(3-Hydroxypropyl)benzonitrile

Participants

Reaction Steps

A 3.27 g (18.7 mmols) quantity of crude 4-(2-hydroxycarbonylethyl)benzonitrile was admixed with 2.86 ml (20.6 mmols) of triethylamine and 40 ml of THF. To the mixture was added 1.96 ml (20.5 mmols) of ethyl chloroformate at 0° C. After stirring the reaction mixture at room temperature for 3 hours, the insolubles were filtered off. The filtrate was concentrated to give a yellow oil, which was then diluted with 100 ml of benzene. The benzene layer was washed with saturated aqueous solution of NaHCO3, dried over Na2SO4 and concentrated to obtain a yelllow oil. This oil was dissolved in 40 ml of THF-water (8:2). To the solution was added 2.13 g (56.1 mmols) of NaBH4 at 0° C. The reaction mixture was stirred at 0° C. for 2 hours and then poured into 100 ml of 3 mol dm-3HCl, followed by extraction with ethyl acetate. The extract was dried over Na2SO4 and concentrated, giving 2.71 g (yield 90%) of 4-(3-hydroxypropyl)benzonitrile in the form of an oil.

Provenance & Evidence