Hydrochloric Acid → 1-[[4-(2-Hydroxyethyl)phenyl]methyl]cyclohexanecarbonitrile

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Reaction Conditions

Reaction Steps

To a mixture maintained under nitrogen, of 5.6 g (54.9 mmoles) of diisopropylamine and 92 ml of dry tetrahydrofuran, cooled to -40° C., there is added dropwise 34.2 ml (54.7 mmoles) of a 1.6M solution of n-butyllithium in hexane, then 8.2 g of 1,3-dimethylimidazolidin-2-one. The mixture is thereafter cooled to -78° C. and is stirred 1/4 hour before adding 5.45 g (50 mmoles) of commercial cyclohexanecarbonitrile in solution in 82 ml of dry tetrahydrofuran. After having stirred 1 hour, at -78° C., 14.3 g (50 mmoles) of the compound prepared in example 26a is added. The temperature is kept for an additional 3 hours at -78° C., before being allowed to rise and the mixture is stirred 19 hours at room temperature. Waster is then added, the mixture is acidified with HCl and is stirred again for 1 hour, before diluting it with water and extracting the reaction mixture with ether. The organic phase, washed with water, dried over Na2SO4 is concentrated. The liquid obtained is purified by distillation to give 7.5 g (yield= 61.6%) of a yellow liquid. b.p.0.5 =130°-80° C.

Provenance & Evidence