Thionyl Chloride → 2-(Trifluoromethyl)prop-2-enoyl chloride

HRID 1380413Notes

Reaction equation

HRID 1380413 reaction equation
S(Cl)([Cl:3])=O.[F:5][C:6]([F:13])([F:12])[C:7](=[CH2:11])[C:8](O)=[O:9]>>[F:5][C:6]([F:13])([F:12])[C:7](=[CH2:11])[C:8]([Cl:3])=[O:9]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 5876942-(Trifluoromethyl)acrylic acid

Product 1

HCID 101490162-(Trifluoromethyl)prop-2-enoyl chlorideYield 66%

Procedure

Thionyl chloride (11.5 ml; 158 mmoles) was added to α-trifluoromethylacrylic acid (19.7 g; 141 mmoles), and the mixture was heated under reflux for 22 hours. Distillation of the reaction mixture under atmospheric pressure gave 14.7 g (yield:66%) of α-trifluoromethylacryloyl chloride, B.p. 89°-90° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 22 hours
  3. distillationDistillation of the reaction mixture under atmospheric pressure

Sources & evidence

ORD record
ord-195be3943dd040cbb074eb4ba395e34a
Source dataset
uspto-grants-1986_04
Patent number
US04581452

Reaction notes

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