3-(Trifluoromethyl)phenol → Ethyl 2-[3-(trifluoromethyl)phenoxy]acetate

A mixture of 100 g (0.618 mole) of α,α,α-trifluoro-m-cresol, 106 g (0.632 mole) of ethyl bromoacetate, 87.5 g (0.632 mole) of potassium carbonate, and 1500 ml of acetone is stirred at reflux for 4 hours, and at room temperature for 18 hours. The mixture is filtered, evaporated under vacuum on a rotorary evaporator at 45° C. and at 85° C. (0.1 mm) to remove excess ethyl bromoacetate. The reaction mixture is taken up in 500 ml of ether, washed three times with 100 ml each of 0.1 M potassium carbonate, once with 100 ml of water, 100 ml of 0.01 M hydrochloric acid, and 100 ml of water. It is then dried with magnesium sulfate, filtered and evaporated, giving 142 g of the crude product. This is fractionally distilled at 73°-75° C. (0.1 mm) to give 124 g of the purified subject product as a colorless liquid.

1. temperatureat reflux for 4 hours
2. filtrationThe mixture is filtered
3. customevaporated under vacuum on a rotorary evaporator at 45° C. and at 85° C. (0.1 mm)
4. customto remove excess ethyl bromoacetate
5. washwashed three times with 100 ml each of 0.1 M potassium carbonate
6. dry with materialIt is then dried with magnesium sulfate
7. filtrationfiltered
8. customevaporated
9. customgiving 142 g of the crude product
10. distillationThis is fractionally distilled at 73°-75° C. (0.1 mm)

ORD record

ord-5335e466498f4caaa150ac978e4bce0f

Source dataset

uspto-grants-1980_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04218566