Sodium Methoxide → 2-(Dimethoxymethyl)-3,3-dimethoxypropanenitrile

HRID 2412449Notes

Reaction equation

HRID 2412449 reaction equation
[CH3:1][O:2][CH:3]=[C:4]([CH:7]([O:10][CH3:11])[O:8][CH3:9])[C:5]#[N:6].[CH3:12][O-:13].[Na+]>C1(C)C=CC=CC=1.CO>[CH3:11][O:10][CH:7]([O:8][CH3:9])[CH:4]([CH:3]([O:13][CH3:12])[O:2][CH3:1])[C:5]#[N:6]

Participants

5

Procedure

In a mixed solvent of 100 ml of toluene and 50 ml of methanol was dissolved 7.85 g (50 mmoles) of 2-methoxymethylene-3,3-dimethoxypropanenitrile. To the resulting solution was added 9.65 g (50 mmoles) of a 28 wt. % solution of sodium methylate in methanol and the mixture was stirred at room temperature for one and a half hours. Subsequently, the reaction mixture was concentrated under reduced pressure to remove the methanol by distillation. To the resulting residue was added 25 ml of water and the toluene layer was separated followed by drying over anhydrous sodium sulfate. The thus dried toluene solution was distilled to obtain 8.50 g (45 mmoles) of 2-dimethoxymethyl-3,3-dimethoxypropanenitrile as a colorless transparent oil boiling at 90°-93° C./2 mmHg.

Workup

  1. concentrationSubsequently, the reaction mixture was concentrated under reduced pressure
  2. customto remove the methanol
  3. distillationby distillation
  4. additionTo the resulting residue was added 25 ml of water
  5. customthe toluene layer was separated
  6. dry with materialby drying over anhydrous sodium sulfate
  7. distillationThe thus dried toluene solution was distilled

Sources & evidence

ORD record
ord-8901c79d5995419da4f9785b4660baac
Source dataset
uspto-grants-1985_01
Patent number
US04492792

Reaction notes

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