Dimethylformamide → Ethyl 4-[3,5-bis(trifluoromethyl)phenoxy]butanoate

HRID 1649300Notes

Reaction equation

[CH:1]1[C:6]([C:7]([F:10])([F:9])[F:8])=[CH:5][C:4]([OH:11])=[CH:3][C:2]=1[C:12]([F:15])([F:14])[F:13].[OH-].[K+].CN(C)C=O.Br[CH2:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28]>C(OCC)C.O>[F:15][C:12]([F:13])([F:14])[C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([C:7]([F:9])([F:8])[F:10])[CH:1]=1)[O:11][CH2:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28]

Participants

Conditions

Temperature: 25 °C

Procedure

To a stirred solution containing 11.5 g (0.05 mole) of 3,5-ditrifluoromethylphenol, 3.3 g (0.05 mole) of 85% potassium hydroxide, 200 ml of N,N-dimethylformamide and 10 ml of water, 0.055 mole of ethyl 4-bromobutyrate was added in one portion. The stirred reaction mixture was heated at 80°-90° C. for 24 hours. After cooling to 25° C., 500 ml of water and 500 ml of ethyl ether were added; and stirring was continued for 15 minutes. The separated ether layer was washed with water until neutral to litmus and dried over sodium sulfate. The ether was removed in vacuo at a maximum temperature of 80°-90° C. at 1-2 mm of Hg. A product with a ND25 =1.4281 was obtained with a 95% yield.

Workup

additionwas added in one portion
customThe stirred reaction mixture
temperaturewas heated at 80°-90° C. for 24 hours
washThe separated ether layer was washed with water until neutral to litmus and
dry with materialdried over sodium sulfate
customThe ether was removed in vacuo at a maximum temperature of 80°-90° C. at 1-2 mm of Hg
customA product with a ND25 =1.4281 was obtained with a 95% yield

Sources & evidence

ORD record: ord-90a43baef6d74f50b2b601f1ea7df2e6
Source dataset: uspto-grants-1983_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04416687

Reaction notes

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