Triethylamine → 4-(3-Hydroxypropyl)benzonitrile

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.

1. filtrationthe insolubles were filtered off
2. concentrationThe filtrate was concentrated
3. customto give a yellow oil, which
4. washThe benzene layer was washed with saturated aqueous solution of NaHCO3
5. dry with materialdried over Na2SO4
6. concentrationconcentrated
7. customto obtain a yelllow oil
8. stirringThe reaction mixture was stirred at 0° C. for 2 hours
9. additionpoured into 100 ml of 3 mol dm-3HCl
10. extractionfollowed by extraction with ethyl acetate
11. dry with materialThe extract was dried over Na2SO4
12. concentrationconcentrated

ORD record

ord-ac2867eb668444e5b6873e04d58359c9

Source dataset

uspto-grants-1985_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04536391