P-Cresol → HCID 18960946, compound

Participants

Reaction Conditions

Reaction Steps

To a cooled (0° C.), stirred solution of 8.4 g (0.15 mole) of potassium hydroxide in 100 ml of MeOH was added 13.5 g (0.12 mole) of 4-methylphenol over a 15 minute period. The reaction was stirred at room temperature for 0.5 hour and MeOH was evaporated to afford a solid. A solution of this solid, 28.2 g (0.1 mole) of ((1-methyl)cyclohexyl)methyl tosylate and 1.4 g of potassium iodide were heated at 150° C. for 5 hours. The reaction was cooled to room temperature, poured onto ice-water and extracted with EtOAc. The EtOAc layer was washed with 2N aqueous NaOH, brine, dried over MgSO4, filtered and evaporated. The resulting oil was filtered through a plug of silica gel to give 20 g of product as an oil.

Provenance & Evidence