2,3-Dimethylbenzaldehyde → (2E)-2-[bis(methyloxy)methyl]-3-(2,3-dimethylphenyl)-2-propenenitrile

HRID 510383Notes

Reaction equation

HRID 510383 reaction equation
[CH2:1]([O:3][CH:4]([O:8][CH2:9]C)[CH2:5][C:6]#[N:7])C.[CH3:11][C:12]1[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][C:13]=1[CH:14]=O.C[O-].[Na+]>CO>[CH3:9][O:8][CH:4]([O:3][CH3:1])/[C:5](=[CH:14]/[C:13]1[CH:16]=[CH:17][CH:18]=[C:19]([CH3:20])[C:12]=1[CH3:11])/[C:6]#[N:7]

Participants

5

Reactant 3

HCID 342242,3-DimethylbenzaldehydeHCID 748513,3-DiethoxypropiononitrileHCID 10942334Sodium Methoxide

Product 1

HCID 86724875(2E)-2-[bis(methyloxy)methyl]-3-(2,3-dimethylphenyl)-2-propenenitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 3,3-bis(ethyloxy)propanenitrile (2.3 g, 20 mmol) and 2,3-dimethylbenzaldehyde (2.1 g, 16 mmol) in methanol (10 mL) was added a 25-30% of sodium methoxide in methanol over 20 minutes. The reaction mixture was stirred at room temperature overnight. Most of solvent was evaporated in vacuo and the residue was dissolved with ethyl acetate (30 mL) and water (15 mL). The two layers were separated. Organic layer was separated, washed with brine (15 mL), dried and concentrated in vacuo. The residue was then purified to give product. It was used in next step. (1.55 g, 33%); 1H NMR (600 MHz, DMSO-d6) δ ppm 2.20 (s, 3H) 2.28 (s, 3H) 3.37 (s, 6H) 5.13 (s, 1H) 7.17-7.22 (m, 1H) 7.27 (d, J=7.55 Hz, 1H) 7.39-7.45 (m, 1H) 7.79 (s, 1H).

Workup

  1. customMost of solvent was evaporated in vacuo
  2. dissolutionthe residue was dissolved with ethyl acetate (30 mL) and water (15 mL)
  3. customThe two layers were separated
  4. customOrganic layer was separated
  5. washwashed with brine (15 mL)
  6. customdried
  7. concentrationconcentrated in vacuo
  8. customThe residue was then purified
  9. customto give product

Sources & evidence

ORD record
ord-53cd88cc1d2a495b9faf0417ee9be0d6
Source dataset
uspto-grants-2015_08
Patent number
US09096605B2

Reaction notes

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