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

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.

1. additionOnce addition
2. temperaturewas heated
3. temperatureto reflux for 3 hours
4. washAt the end of this time the mixture was washed with 10% sodium carbonate (150 ml), water (150 ml)
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationThe mixture was then filtered
7. customthe solvents were evaporated under reduced pressure
8. customto afford a clear yellow liquid
9. distillationThe material was distilled on a Kugelrohr distillation apparatus at 140° C.

ORD record

ord-494a8fad91374457b4567453d4ccad1b

Source dataset

uspto-grants-1998_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05747523