Thionyl Chloride → HCID 19363243, compound

Participants

Reaction Steps

N-(2-Hydroxy-1,1-dimethylethyl)-4-methoxy-3-pentyloxybenzamide (5.498 g, 0.0178 mol, 1 eq) was dissolved in thionyl chloride (4.29 ml, 0.0214 mol, 3.3 eq), and the solution was stirred at room temperature for 1 hour. The reaction mixture was poured into diethyl ether (40 ml). The obtained hydrochloride compound was collected by filtration, and excess thionyl chloride was removed. A 1N aqueous sodium hydroxide solution (about 20 ml) was added to this hydrochloride compound under ice-cooling, whereby the mixture was alkalized (pH=10). The solution was extracted twice with diethyl ether (30 ml). The organic layers were combined, washed with saturated brine (60 ml) and dried over anhydrous sodium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure to give 2-(4-methoxy-3-pentyloxyphenyl)-4,4-dimethyl-4,5-dihydrooxazole (4.46 g, 86%) as colorless crystals.

Provenance & Evidence