Toluene → alpha-Formyl-3-(trifluoromethyl)benzeneacetonitrile

HRID 1733579Notes

Reaction equation

HRID 1733579 reaction equation
C[O-].[Na+].C1(C)C=CC=CC=1.[CH:11](OCC)=[O:12].[F:16][C:17]([F:28])([F:27])[C:18]1[CH:19]=[C:20]([CH2:24][C:25]#[N:26])[CH:21]=[CH:22][CH:23]=1>O>[CH:11]([CH:24]([C:20]1[CH:21]=[CH:22][CH:23]=[C:18]([C:17]([F:27])([F:28])[F:16])[CH:19]=1)[C:25]#[N:26])=[O:12]

Participants

6

Reactant 4

HCID 1140Toluene2×HCID 8025Ethyl formateHCID 75360m-TrifluoromethylphenylacetonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 13133052alpha-Formyl-3-(trifluoromethyl)benzeneacetonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a slurry of 30.0 g. of sodium methoxide in 1200 ml. of toluene and 43.4 g. of ethyl formate is added dropwise with stirring 98.75 g. of 3-(trifluoromethyl)benzeneacetonitrile in 75 ml. of toluene over a 10 minute period. The temperature of the mixture rises to 35° C. and the mixture thickens. Stirring is continued for 2 hours and then one liter of water is added. The aqueous layer is acidified and a precipitate is formed by scratching to give 85.0 g. of the product of the Example as a white solid, m.p. 103°-106.5° C.

Workup

  1. customrises to 35° C.
  2. stirringStirring
  3. customa precipitate is formed
  4. customto give 85.0 g

Sources & evidence

ORD record
ord-916c7454a2ac4cdcb375dfa08a203dbe
Source dataset
uspto-grants-1980_12
Patent number
US04242515

Reaction notes

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