3-Benzoyloxycyclohexene (CAS NO.: ), which is also known as 2-Cyclohexen-1-ol, benzoate, could be produced through the following synthetic routes.

A 250-ml., three-necked, round-bottomed flask equipped with a sealed mechanical stirrer, a reflux condenser, and a pressure-equalizing dropping funnel is set up for conducting a reaction in an atmosphere of nitrogen by fitting into the top of the condenser a T-tube attached to a low-pressure supply of nitrogen and to a mercury bubbler. In the flask are placed 41 g. (0.50 mole) of cyclohexene and 0.05 g. (0.00035 mole) of cuprous bromide, and the mixture is heated in an oil bath at 80–82°. When the temperature of the mixture reaches that of the oil bath, 40 g. (0.21 mole) of t-butyl perbenzoate is added dropwise with stirring over a 1-hour period, during which the color of the now homogeneous solution becomes blue. Stirring and heating are continued for an additional 3.5 hours. The cooled reaction mixture is washed with two 50-ml. portions of dilute aqueous sodium carbonate to remove benzoic acid. The remaining organic phase is washed with water until neutral and dried over anhydrous sodium sulfate. The excess of cyclohexene is removed by distillation under reduced pressure, and the residue is distilled through a short Vigreux column to give 29–33 g. (71–80%) of 3-benzoyloxycyclohexene, b.p. 97–99° (0.15 mm.), n²⁰D 1.5376–1.5387.

Notice: This reaction should be carried out behind a safety screen. The solvent removal and product distillation steps should also be carried out behind a screen to minimize danger due to contamination of the product with undetected peroxides.