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Under a dry argon atmosphere a mixture of 10.0 g (0.084 mole) of 4-cyanophenol, 33.6 g (0.84 mole) of sodium hydroxide, 110 ml of water, and 130 ml of tetrahydrofuran was stirred in a Morton flask and heated at reflux. During 1.25 hour, 8.6 g (0.99 mole) of chlorodifluoromethane was added to the reaction mixture. After complete addition, the mixture was allowed to cool to room temperature and was stirred for approximately 18 hours. The reaction mixture was poured into 500 g of ice water, the resulting mixture filtered, and the filtrate extracted with three 300 ml portions of diethyl ether. The ether extracts were combined, dried over anhydrous potassium carbonate, and filtered. The filtrate was evaporated under reduced pressure to give an oil which crystallized upon standing. The product was recrystallized from toluene/methylcyclohexane to give 5.2 g of 4-difluoromethoxybenzonitrile as a white solid, m.p. 36°-37° C.

1. temperatureheated
2. temperatureat reflux
3. additionAfter complete addition
4. stirringwas stirred for approximately 18 hours
5. filtrationthe resulting mixture filtered
6. extractionthe filtrate extracted with three 300 ml portions of diethyl ether
7. dry with materialdried over anhydrous potassium carbonate
8. filtrationfiltered
9. customThe filtrate was evaporated under reduced pressure
10. customto give an oil which
11. customcrystallized
12. customThe product was recrystallized from toluene/methylcyclohexane