[OH-].[Na+].[Cl-].[Na+].[C:5]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)([CH3:7])=[CH2:6].[CH3:15]I>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl.O>[C:5]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)([CH3:7])=[CH2:6]
A two-liter reaction flask was charged with 375 mls of water, 18.25 gms of sodium hydroxide, 125 mls of saturated sodium chloride, 50 gms of para-isopropenylphenol, 450 cc of methylene chloride, 7.5 gms of tetrabutylammoniumbromide, and 35 mls of methyl iodide. The reaction flask was flushed with nitrogen, and the mixture was stirred overnight. The phases were separated, and the aqueous phase was washed with methylene chloride. The combined organic layers were washed with 5% sodium hydroxide and saturated sodium chloride. The solution was dried over sodium sulfate. The methylene chloride was removed by distillation, and 400 mls of diethyl ether was added to precipitate the phase transfer catalyst. After filtration, the ether was stripped and the residue was distilled to give 25 gms of para-isopropenylanisole for a yield of 45%.
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