tert-Butanol → Trifluoroacetic acid

HRID 1389752Notes

Reaction equation

HRID 1389752 reaction equation
[C:1](#[N:4])[CH:2]=[CH2:3].[CH:5]1[C:18]2[NH:17]C3C(=CC=CC=3)SC=2C=C[CH:6]=1.[C:19](O)([CH3:22])([CH3:21])[CH3:20].[F:24][C:25]([F:30])([F:29])[C:26]([OH:28])=[O:27]>>[C:1](#[N:4])[CH:2]=[CH2:3].[F:24][C:25]([F:30])([F:29])[C:26]([OH:28])=[O:27].[C:19]([NH:17][C:18](=[O:27])[CH:5]=[CH2:6])([CH3:22])([CH3:21])[CH3:20]

Participants

7

Reactant 4

HCID 6386tert-ButanolHCID 6422Trifluoroacetic acidHCID 7108PhenothiazineHCID 7855Acrylonitrile

Product 3

HCID 6422Trifluoroacetic acidHCID 7855AcrylonitrileHCID 7877tert-Butylacrylamide

Procedure

84 g of acrylonitrile are added dropwise to a solution of 1 g of phenothiazine in 90 g of trifluoroacetic acid at 20° C., whilst stirring. Thereafter, 43 g of tert.-butanol are added dropwise at 35° C. The reaction mixture is kept at 60° to 70° C. for 6 hours and then worked up by distillation. Acrylonitrile, trifluoroacetic acid and some of the N-tert.-butylacrylamide formed are distilled off under reduced pressure. 36 g of N-tert.-butylacrylamide (melting point 120° to 122° C.) remain as the distillation bottom product. The distillate can be re-used in the reaction with the same result.

Workup

  1. distillationworked up by distillation

Sources & evidence

ORD record
ord-c3e7a1b1f2b24d75a824b165907cc7af
Source dataset
uspto-grants-1981_01
Patent number
US04246199

Reaction notes

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