Methanol → 4-(3-Ethynylphenoxy)naphthalic anhydride

Participants

Reaction Conditions

Reaction Steps

To 100 ml of anhydrous methanol was added 20 g (0.073 mole) of 3-ethynylphenyl(p-toluenesulfonate) and 8.19 g (0.146 mole) of potassium hydroxide. The mixture was heated to reflux, under a nitrogen atmosphere and maintained at reflux for four hours. The methanol solvent was removed in vacuo at 40° C. by means of a rotary evaporator, leaving a dry, white powder. The white powder was dissolved in 100 ml of dimethylsulfoxide (DMSO) and added dropwise to a DMSO solution containing 13.8 g (0.05 mole) of 4-bromonaphthalic anhydride at 90° C. The mixture was heated at 100° C., under a nitrogen atmosphere, for 12 hours. The reaction mixture was allowed to cool to room temperature and poured into diethylether to precipitate the inorganic salts which were removed by filtration. The diethylether/DMSO solvent was removed in vacuo at 90° C., by means of a rotary evaporator leaving a residual oil. The oil was dissolved in methylene chloride and filtered through a 2""×6" dry column of silica gel while eluting the column with methylene chloride. The eluate was evaporated to dryness, yielding 7.8 g (50%) of 4-(3-ethynylphenoxy)naphthalic anhydride.

Provenance & Evidence