2-Chloroethanol → 1-[Bis(4-fluorophenyl)methoxy]-2-chloroethane

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Reaction Steps

2-Chloroethanol (2) (4.1 g, 51 mmol) was added to a 500 ml three neck round bottom flask containing 250 ml of toluene and sulfuric acid(1 ml, 18 mmol). A solution of 4,4'-difluorobenzhydrol (1) (9.16 g, 41.6 mmol) in 50 ml of toluene was then added dropwise over 30 minutes. Once addition was complete the resulting mixture was heated to reflux for 3 hours. At the end of this time the mixture was washed with 10% sodium carbonate (150 ml), water (150 ml), and dried over anhydrous magnesium sulfate. The mixture was then filtered and the solvents were evaporated under reduced pressure to afford a clear yellow liquid. The material was distilled on a Kugelrohr distillation apparatus at 140° C., 0.5 mm Hg to afford the desired product (3) (7.0 g, 60%) as a clear and colorless liquid which crystallized slowly upon standing.

Provenance & Evidence