Hydroquinone → 2,2,3,4,4,4-Hexafluorobutyl alpha-fluoroacrylate

HRID 1460849Notes

Reaction equation

HRID 1460849 reaction equation
[F:1][C:2]([F:17])([CH:11]([F:16])[C:12]([F:15])([F:14])[F:13])[CH2:3][O:4][C:5](=[O:10])[CH:6]([F:9])[CH2:7]F.C1(C=CC(O)=CC=1)O.N12CCCC1=NCCC2>C(OCC)C>[F:9][C:6](=[CH2:7])[C:5]([O:4][CH2:3][C:2]([F:1])([F:17])[CH:11]([F:16])[C:12]([F:15])([F:14])[F:13])=[O:10]

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 763491,5-Diazabicyclo(4.3.0)non-5-eneHCID 147165092,2,3,4,4,4-Hexafluorobutyl 2,3-difluoropropanoate

Product 1

HCID 147165102,2,3,4,4,4-Hexafluorobutyl alpha-fluoroacrylateYield 45.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 55.5 g (0.2 mole) of 2,3-difluoropropionic acid-2,2,3,4,4,4-hexafluorobutylester and a spatula tipful of hydroquinone in 550 ml of dry diethyl ether there was added dropwise at -10° C. a solution of 23 g (0.19 mole) of 1,5-diazabicyclo[4.3.0]non-5-ene in 140 ml of dry diethyl ether. The solvent was then distilled off in vacuo in the cold and the residue remaining was fractionated. In this way, 23 g of 2,2,3,4,4,4-hexafluorobutyl α-fluoroacrylate were obtained having a boiling point of 53° to 54° C. at 20 mbar and a purity of 98%.

Workup

  1. distillationThe solvent was then distilled off in vacuo in the cold and the residue

Sources & evidence

ORD record
ord-1194d1dbf57d4c91bbcd0158708e0955
Source dataset
uspto-grants-1991_12
Patent number
US05072030

Reaction notes

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