2-Benzylidenecyclohexanone → 2-Benzylphenol

Participants

Reaction Conditions

Reaction Steps

In a 100-ml, four-necked flask equipped with a magnetic stirrer, a reflux condenser and a thermometer were placed 18.6 g (0.1 mole) of the 2-benzylidenecyclohexanone produced in Example 1 and 51.7 g (0.3 mole) of diethyl maleate in this order. The flask inside was purged with nitrogen. Thereto was added 1.9 g (10 wt. %, 0.89 mmole as palladium) of 5% palladium carbon (a product of Wako Pure Chemical Industries, Ltd.). The system was made vacuum using an aspirator and then returned to ordinary pressure using nitrogen; this operation was repeated three times. Then, the system was stirred at 185° C. for 3 hours and cooled to room temperature. 100 ml of toluene was added to the system. Filtration was conducted to remove the palladium carbon. The filtrate was extracted with 100 ml of a 10% aqueous sodium hydroxide solution, and this operation was repeated four times. The aqueous layer was washed with 30 ml of toluene. To the resulting aqueous layer was added 35% hydrochloric acid until the aqueous layer became acidic, after which the aqueous layer was extracted with 100 ml of toluene. The toluene layer was washed with water and a saturated aqueous sodium chloride solution in this order. The toluene layer was dried over anhydrous sodium sulfate and then subjected to vacuum distillation to remove toluene, to obtain 10.7 g of an oil. This oil was subjected to Kugel Rohr distillation to obtain 9.0 of a colorless oil. Yield: 49% The purity of the intended product in the oil was >99.9% as measured by gas chromatography.

Provenance & Evidence