Methacryloyl chloride → 5,5,5-Trifluoro-4-hydroxy-4-(trifluoromethyl)pentan-2-yl methacrylate

HRID 1744182

Reaction equation

[C:1]([O-:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].[F:7][C:8]([F:20])([F:19])[C:9]([C:15]([F:18])([F:17])[F:16])([OH:14])[CH2:10][CH:11](O)[CH3:12].C([Li])CCC.C(Cl)(=O)C(C)=C>>[C:1]([O:6][CH:11]([CH3:12])[CH2:10][C:9]([C:8]([F:7])([F:19])[F:20])([OH:14])[C:15]([F:16])([F:18])[F:17])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

Reactant 4

HCID 13528Methacryloyl chloride

HCID 87595Methacrylate

HCID 1181911,1,1-Trifluoro-2-(trifluoromethyl)-2,4-pentanediol

HCID 178418339Butyllithium

Product 1

HCID 160501385,5,5-Trifluoro-4-hydroxy-4-(trifluoromethyl)pentan-2-yl methacrylate

Procedure

The title compound was prepared in the same fashion as the above described methacrylate using 142 g (0.63 mol) of 1,1,1-trifluoro-2-trifluoromethyl-2,4-pentanediol, 793 mL (1.27 mol) of n-butyllithium (1.6M in hexane) and 73 g (0.69 mol) of methacryloyl chloride to yield, after distillation at 67° C. at 1.0 mm Hg, 142 g (76%) of the 2° methacrylate as a clear, colorless oil.

Workup

customto yield
distillationafter distillation at 67° C. at 1.0 mm Hg, 142 g (76%) of the 2° methacrylate as a clear, colorless oil

Sources & evidence

ORD record: ord-76a0cc962c414740b24ca14b0b684469
Source dataset: uspto-grants-2006_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07014980B2

Linked notes

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