Triethylamine → 2-(3,4-Dimethylphenyl)-hexafluoro-2-propyl alpha-fluoroacrylate

HRID 1614790Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([C:9]([OH:18])([C:14]([F:17])([F:16])[F:15])[C:10]([F:13])([F:12])[F:11])[CH:5]=[CH:6][C:7]=1[CH3:8].C(N(CC)CC)C.[F:26][C:27](=[CH2:31])[C:28](Cl)=[O:29]>C(OCC)C>[F:26][C:27](=[CH2:31])[C:28]([O:18][C:9]([C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([CH3:1])[CH:3]=1)([C:10]([F:11])([F:12])[F:13])[C:14]([F:17])([F:15])[F:16])=[O:29]

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of 27.3 g (0.1 mol) Of 2-(3,4-dimethylphenyl)-hexafluoro-2-propanol and 10.1 g (0.1 mol) of triethylamine in 50 ml of dry diethyl ether was added dropwise with stirring at a temperature of 20° C. to a solution of 20 g (0.184 mol) of α-fluoroacryloyl chloride (obtained according to Example 4) in 50 ml of dry diethyl ether in the course of 35 minutes. The reaction mixture was then stirred at a temperature of 20° C. for a further 3.5 hours. The resulting solid was filtered off. The filtrate was distilled under reduced pressure after addition of 0.01 g of hydroquinone monomethyl ether. 17.7 g (51 percent of theory) of 2-(3,4-dimethylphenyl)-hexafluoro-2-propyl α-fluoroacrylate having a boiling point of 72° to 73° C. (under 0.4 mbar) were obtained.

Workup

filtrationThe resulting solid was filtered off
distillationThe filtrate was distilled under reduced pressure
additionafter addition of 0.01 g of hydroquinone monomethyl ether

Sources & evidence

ORD record: ord-721cf85334564ec9b439150cfb1efb78
Source dataset: uspto-grants-1993_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05198925

Reaction notes

Loading…