Potassium Hydroxide → 3-[4-Chloro-3-(trifluoromethyl)phenyl]prop-2-enenitrile

HRID 1491972Notes

Reaction equation

HRID 1491972 reaction equation
[C:1]([CH2:3]P(=O)(OCC)OCC)#[N:2].[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][C:14]=1[C:21]([F:24])([F:23])[F:22].[OH-].[K+]>O1CCCC1>[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[CH:3][C:1]#[N:2])=[CH:15][C:14]=1[C:21]([F:22])([F:23])[F:24]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 1186424-Chloro-3-(trifluoromethyl)benzaldehyde

Product 1

HCID 541762263-[4-Chloro-3-(trifluoromethyl)phenyl]prop-2-enenitrileYield 87.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 10.6 g (0.06 mol) of diethyl cyanomethylphosphonate and 12.5 g (0.06 mol) of 4-chloro-3trifluoromethyl-benzaldehyde in 65 ml of tetrahydrofuran is added dropwise to a suspension of 6.7 g (0.12 mol) of pulverulent potassium hydroxide in 185 ml of tetrahydrofuran. During this process the temperature of the reaction mixture rises slightly. Stirring is subsequently continued at room temperature for 20 minutes, and the solid which separates out in this process is filtered off and washed with tetrahydrofuran. The filtrate is concentrated in vacuo and the residue which remains is dried. 12.1 g (87.0% of theory) of 4-chloro-3-trifluoromethyl-cinnamonitrile are obtained in the form of an E/Z isomer mixture.

Workup

  1. filtrationis filtered off
  2. washwashed with tetrahydrofuran
  3. concentrationThe filtrate is concentrated in vacuo
  4. customthe residue which remains is dried

Sources & evidence

ORD record
ord-628ad8eb444843a2b570afb1be9bcd94
Source dataset
uspto-grants-1994_12
Patent number
US05371231

Reaction notes

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