Ethyl formate → alpha-Formyl-4-benzylphenylacetonitrile

HRID 439777Notes

Reaction equation

HRID 439777 reaction equation
C[O-].[Na+].[CH:4](OCC)=[O:5].[CH2:9]([C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]#[N:24])=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1(C)C=CC=CC=1>[CH:4]([CH:22]([C:19]1[CH:18]=[CH:17][C:16]([CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:21][CH:20]=1)[C:23]#[N:24])=[O:5]

Participants

5

Reactant 3

HCID 8025Ethyl formateHCID 5975314-BenzylphenylacetonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 15280468alpha-Formyl-4-benzylphenylacetonitrileYield 70.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspention of sodium methoxide (64.26 g) in toluene (2.5 l) was added dropwise at 0° C. a mixture of ethyl formate (88.14 g) and 4-benzylphenylacetonitrile (189.69 g) with stirring. After 30 minutes, ice bath was removed. After 20 hours, ice water (2.6 l) was added to the reaction mixture, and the aqueous layer was separated. The organic layer was washed with 0.5N sodium hydroxide aqueous solution (500 ml×5). The aqueous layer and the washings were combined, adjusted to acid with conc. hydrochloric acid, and stirred at 0° C. for 30 minutes. The precipitate was separated by filtration, washed, and dried to give the title compound (152.22 g).

Workup

  1. customice bath was removed
  2. waitAfter 20 hours
  3. additionice water (2.6 l) was added to the reaction mixture
  4. customthe aqueous layer was separated
  5. washThe organic layer was washed with 0.5N sodium hydroxide aqueous solution (500 ml×5)
  6. stirringstirred at 0° C. for 30 minutes
  7. customThe precipitate was separated by filtration
  8. washwashed
  9. customdried

Sources & evidence

ORD record
ord-30133cff454b485494fd48dacb97e0fe
Source dataset
uspto-grants-1996_05
Patent number
US05516777

Reaction notes

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