Water → 2-Hydroxy-3-(trifluoromethyl)benzonitrile

HRID 1580560Notes

Reaction equation

HRID 1580560 reaction equation
[N+]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]([F:13])([F:12])[F:11])([O-])=O.[C-:14]#[N:15].[K+].[OH2:17]>CS(C)=O>[F:11][C:10]([F:13])([F:12])[C:5]1[CH:6]=[CH:7][CH:8]=[C:9]([C:14]#[N:15])[C:4]=1[OH:17]

Participants

5

Reactant 3

HCID 962WaterHCID 9032Potassium CyanideHCID 97952-Nitro-alpha,alpha,alpha-trifluorotoluene

Product 1

HCID 215629922-Hydroxy-3-(trifluoromethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-Nitro-α,α,α-trifluorotoluene (3.82 g.) was heated at 100°C for 3 hours with potassium cyanide (7.8 g.) in dimethyl sulphoxide (40 ml.). After pouring into water, the mixture was brought to pH 7 and filtered. Acidification, ether extraction, and removal of the ether gave a solid which was sublimed or crystallised from aqueous ethanol to give 3-trifluoromethyl-salicylonitrile, m.p. 134°C.

Workup

  1. filtrationfiltered
  2. extractionAcidification, ether extraction, and removal of the ether
  3. customgave a solid which
  4. customcrystallised from aqueous ethanol

Sources & evidence

ORD record
ord-67a5dc71bf47436a822058a833a62bc5
Source dataset
uspto-grants-1976_01
Patent number
US03933807

Reaction notes

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