Formaldehyde → o-(Trifluoromethyl)styrene

HRID 904768Notes

Reaction equation

HRID 904768 reaction equation
[Cl-].[F:2][C:3]([F:31])([F:30])[C:4]1[CH:29]=[CH:28][CH:27]=[CH:26][C:5]=1[CH2:6][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH2:32]=O.[OH-].[Na+]>O>[F:31][C:3]([F:2])([F:30])[C:4]1[CH:29]=[CH:28][CH:27]=[CH:26][C:5]=1[CH:6]=[CH2:32]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 20477565o-Trifluoromethylbenzyltriphenyl-phosphonium chloride

Product 1

HCID 2778198o-(Trifluoromethyl)styrene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

457 g (1 mol) of o-trifluoromethylbenzyltriphenyl-phosphonium chloride and 150 g (5 mols) of paraformaldehyde are initially introduced into 1,200 ml of water. 150 ml of 50% strength by weight sodium hydroxide solution are added at about 20° C. The mixture is allowed to after-react at 40° to 50° C. for 1 hour and the o-trifluoromethylstyrene formed is then distilled out of the reaction mixture with steam. The organic phase of the distillate contains 170 g (about 98% of the theoretical yield) of o-trifluoromethylstyrene with a purity, according to analysis by gas chromatography, of 99%. nD20 :1.4663. Boiling point: 61° C. under 53 mbars.

Workup

  1. customto after-react at 40° to 50° C. for 1 hour

Sources & evidence

ORD record
ord-9f83ea98cbb64914afc157358b25d9e4
Source dataset
uspto-grants-1983_12
Patent number
US04420225

Reaction notes

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