Chloroacetaldehyde → 2-(2,3,6-Trimethylanilino)acetaldehyde

HRID 1658960Notes

Reaction equation

HRID 1658960 reaction equation
[CH3:1][C:2]1[C:8]([CH3:9])=[CH:7][CH:6]=[C:5]([CH3:10])[C:3]=1[NH2:4].Cl[CH2:12][CH:13]=[O:14].C(=O)([O-])[O-].[Na+].[Na+]>>[CH3:1][C:2]1[C:8]([CH3:9])=[CH:7][CH:6]=[C:5]([CH3:10])[C:3]=1[NH:4][CH2:12][CH:13]=[O:14]

Participants

4

Reactant 3

HCID 33ChloroacetaldehydeHCID 10340Sodium CarbonateHCID 119589472,3,6-Trimethylaniline

Product 1

HCID 214128082-(2,3,6-Trimethylanilino)acetaldehyde

Conditions

Temperature
150 °C

Procedure

2,3,6-Trimethylaniline (0.3 mole), the dimethyl acetal of 2-chloroacetaldehyde (0.3 mole) and sodium carbonate (20 grams) are charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture is heated at about 150°C for a period of about 8 hours. After this time the mixture is filtered and the filtrate is distilled to yield the desired product the dimethyl acetal of 2-(2,3,6-trimethylanilino)acetaldehyde.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturethermometer and reflux condenser
  3. filtrationAfter this time the mixture is filtered
  4. distillationthe filtrate is distilled

Sources & evidence

ORD record
ord-1478eaf2490d4114908b8a292dbbdc56
Source dataset
uspto-grants-1976_06
Patent number
US03966811

Reaction notes

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