4-Ethenylphenyl acetate → 4-Vinylphenol

Participants

Reaction Conditions

Reaction Steps

100.00 parts by mass of p-acetoxystyrene was dissolved in 400 parts by mass of ethyl acetate and cooled to 0° C., and 47.60 parts by mass of sodium methoxide (28% methanol solution) was added dropwise to the cooled solution over a period of 30 minutes, followed by stirring at room temperature for 5 hours. Ethyl acetate was added thereto and the organic layer was washed with distilled water three times. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off to obtain 131.70 parts by mass of p-hydroxystyrene (54% ethyl acetate solution). 18.52 parts by mass of the p-hydroxystyrene (54% ethyl acetate solution) was dissolved in 56.00 parts by mass of ethyl acetate, and 31.58 parts by mass of 1,1,2,2,3,3-hexafluoropropane-1,3-disulfonyl difluoride was added thereto, followed by cooling to 0° C. A solution obtained by dissolving 12.63 parts by mass of triethylamine in 25.00 parts by mass of ethyl acetate was added dropwise to the mixture over a period of 30 minutes, followed by stirring while cooling at 0° C. for 4 hours. Ethyl acetate was added thereto, the organic layer was washed with saturated saline three times, and then dried over anhydrous sodium sulfate. The solvent was evaporated, and then the residue was dissolved in 315 parts by mass of methanol, followed by cooling to 0° C. 245 parts by mass of a 1 N aqueous sodium hydroxide solution was added thereto, followed by stirring at room temperature for 2 hours. The solvent was evaporated, followed by addition of ethyl acetate. The organic layer was washed with saturated saline three times, and then dried over anhydrous sodium sulfate. The solvent was evaporated, and then the residue was dissolved in 200 parts by mass of methanol. 27.22 parts by mass of triphenylsulfonium bromide was added thereto, followed by stirring at room temperature for 3 hours. The solvent was evaporated, followed by extraction with chloroform three times. The resultant organic layer was washed with saturated saline three times and then the solvent was evaporated to obtain 50.55 parts by mass of a desired compound (M-I-1).

Provenance & Evidence