Hydrochloric Acid → rac-(2S*)-2-[(R*)-3,4-dichloro-alpha-(nitromethyl)benzyl]cyclohexanone

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Reaction Steps

A solution of 52.3 g (0.24 mol) of 3,4-dichloro-ω-nitrostyrene in 500 ml of methylene chloride is added while stirring and cooling within about 45 minutes to a solution of 40.1 g (0.24 mol) of N-(1-cyclohexen-1-yl)morpholine in 400 ml of methylene chloride under nitrogen so that the temperature does not exceed 0°. The mixture is subsequently stirred at 0° for a further 3 hours. 420 ml of 1N hydrochloric acid are added rapidly while stirring intensively, whereupon the mixture is stirred for a further 30 minutes. The aqueous phase is separated and extracted twice with 500 ml of methylene chloride each time; the organic phase is washed with water, dried over magnesium sulphate and evaporated. The oily residue obtained is taken up in 250 ml of isopropyl ether and left to stand in a refrigerator overnight. There is obtained rac-(2S*)-2-[(R*)-3,4-dichloro-α-(nitromethyl)benzyl]cyclohexanone in the form of colourless crystals of m.p. 109°- 110°.

Provenance & Evidence