2-Chloroethanol → 2-[2-(2,2,2-Trifluoroethoxy)phenoxy]ethanol

Temperature

102.5 °C

To a mixture of 2-(2,2,2-trifluoroethoxy)phenol (XI) (6 g, 0.03 mole), N,N-dimethylformamide (50 ml) and potassium carbonate (13.0 g, 0.09 mole) was added 2-chloroethanol (4.2 ml, 0.06 mole). Reaction mixture was heated to 100-105° C. and stirred for 10 hours. Reaction mass was filtered and the filtrate was concentrated under reduced pressure to distill out the N,N-Dimethyl formamide. To the residue was added water and product was extracted in ethyl acetate (50 ml). The organic layer was washed with water and dried over sodium sulphate. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography on silica gel using a mixture of ethyl acetate and hexane (5/95) as eluent to give 4.0 g of (XIV) as oil. Purity (By GC)=95%

1. customReaction mixture
2. customReaction mass
3. filtrationwas filtered
4. concentrationthe filtrate was concentrated under reduced pressure
5. distillationto distill out the N,N-Dimethyl formamide
6. additionTo the residue was added water and product
7. extractionwas extracted in ethyl acetate (50 ml)
8. washThe organic layer was washed with water
9. dry with materialdried over sodium sulphate
10. customThe solvent was evaporated under reduced pressure
11. customthe residue was purified by column chromatography on silica gel using
12. additiona mixture of ethyl acetate and hexane (5/95) as eluent

ORD record

ord-a15e75350f294621a8501bb4e224594e

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08471039B2