Benzaldehyde → 2-(Dimethoxymethyl)-3-phenylacrylonitrile

HRID 496819Notes

Reaction equation

HRID 496819 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][O:10][CH:11]([O:15][CH3:16])[CH2:12][C:13]#[N:14].C[O-].[Na+]>CO>[CH3:9][O:10][CH:11]([O:15][CH3:16])[C:12](=[CH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:13]#[N:14]

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 937313,3-DimethoxypropiononitrileHCID 10942334Sodium Methoxide

Product 1

HCID 538099012-(Dimethoxymethyl)-3-phenylacrylonitrileYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Benzaldehyde (79.5 g, 0.75 mol) and 3,3-dimethoxypropionitrile (115.1 g, 1.0 mol) were mixed together and added to a solution of sodium methoxide (54.0 g, 1.0 mol) in methanol (400 mL) over a period of 15 minutes. The mixture was stirred at room temperature overnight. Most of the methanol was evaporated in vacuo and the residue was partitioned between ethyl acetate (500 mL) and water (450 mL). The organic layer was separated, washed with brine (400 mL), dried (MgSO4) and the solvent evaporated in vacuo. The residual oil was distilled to give 103 g (68%) of the product as a colorless oil, bp 125-130° C. (2 mm Hg).

Workup

  1. customMost of the methanol was evaporated in vacuo
  2. customthe residue was partitioned between ethyl acetate (500 mL) and water (450 mL)
  3. customThe organic layer was separated
  4. washwashed with brine (400 mL)
  5. dry with materialdried (MgSO4)
  6. customthe solvent evaporated in vacuo
  7. distillationThe residual oil was distilled

Sources & evidence

ORD record
ord-2dbbaa9df03f4353865da47aa9bc6ae9
Source dataset
uspto-grants-2005_09
Patent number
US06946554B2

Reaction notes

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