Benzoic Acid → HCID 86602886, compound

Participants

Reaction Steps

To a solution of benzoic acid (1.1 g, 8.8 mmol) and PS-triphenylphosphine (6.7 g, 15.5 mmol) in anhydrous THF (40 mL) was added cis-3-hydroxy-cyclohexanecarbonitrile (1.1 g, 8.8 mmol) in anhydrous THF (20 mL). The reaction mixture was cooled while diethyl azodicarboxylate (DEAD) (1.9 mL, 12.3 mmol) was added by syringe over 3 min. The reaction was shaken for 12 h. The mixture was filtered and the resin was washed with ether. The filtrate was concentrated in vacuo to afford an oily solid. Silica gel column chromatography using 95:5 hexanes:EtOAc as an eluent afforded 0.29 g (14%) of benzoic acid trans-3-cyano-cyclohexyl ester as a white solid.

Provenance & Evidence