4-Nitrobenzoic Acid → HCID 86742923, compound

Participants

Reaction Steps

9.1 g (32.1 mmol) of rac-(1S*)-cis-2-[(R*)-4-chloro-α-(nitromethyl)benzyl]cyclohexanol, 16.8 g (64.2 mmol) of triphenylphosphine and 10.8 g (64.2 mmol) of p-nitrobenzoic acid are dissolved in 180 ml of tetrahydrofuran. To this solution is added dropwise with 30 minutes a solution of 11.3 g (64.2 mmol) of diethyl azodicarboxylate in 80 ml of tetrahydrofuran and the mixture is subsequently stirred at room temperature for 5 hours. After distilling off the solvent the residue obtained is chromatographed on a 30-fold amount of silica gel while eluting with toluene/hexane (1:2). By recrystallization of the product obtained from methylene chloride/hexane there is obtained rac-(1R*)-trans-2-[(R*)-4-chloro-α-(nitromethyl)benzyl]cyclohexyl p-nitrobenzoate in the form of colourless crystals of m.p. 146°-148°.

Provenance & Evidence