Dimethyl Sulfate → HCID 19363464, compound

Participants

Reaction Conditions

Reaction Steps

1-(2-Hydroxy-5-methylphenyl)heptan-1-one (127 g, 0.61 mol), a 2.5N aqueous sodium hydroxide solution (250 ml) and ethanol (250 ml) were mixed, and this solution was cooled to 0° C. Dimethyl sulfate (60 ml) was added, and the mixture was refluxed under heating for 2 hours. Dimethyl sulfate (40 ml) and a 2.5N aqueous sodium hydroxide solution (170 ml) were further added, and the mixture was refluxed under heating for 2 hours. The reaction mature was concentrated under reduced pressure and the obtained residue was extracted twice with ether (200 ml). The organic layers were combined, washed twice with a 2.5N aqueous sodium hydroxide solution and saturated brine (100 ml1 each), and dried over anhydrous magnesium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography (n-hexane/ethyl acetate=95/5) to give 1-(2-methoxy-5-methylphenyl)heptan-1-one (82 g, 57%) as a colorless oil.

Provenance & Evidence