Chloroacetaldehyde → 2-(2,6-Diethylanilino)acetaldehyde

HRID 1576935Notes

Reaction equation

HRID 1576935 reaction equation
[CH2:1]([C:3]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][CH3:11])[C:4]=1[NH2:5])[CH3:2].Cl[CH2:13][CH:14]=[O:15].C(=O)([O-])[O-].[Na+].[Na+]>>[CH2:1]([C:3]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][CH3:11])[C:4]=1[NH:5][CH2:13][CH:14]=[O:15])[CH3:2]

Participants

4

Reactant 3

HCID 33ChloroacetaldehydeHCID 10340Sodium CarbonateHCID 113692,6-Diethylaniline

Product 1

HCID 214128262-(2,6-Diethylanilino)acetaldehyde

Conditions

Temperature
150 °C

Procedure

2,6-Diethylaniline (100 grams), the dimethyl acetal of 2-chloroacetaldehyde (37.5 grams) and sodium carbonate (31.8 grams) were charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The mixture was heated at a temperature of about 150°C for a period of about 30 hours. After this time the reaction mixture was cooled to room temperature and was filtered. The filtrate was then distilled under vacuum to yield the desired product the dimethyl acetal of 2-(2,6-diethylanilino)acetaldehyde as the residue having a boiling point of 120°C at 1 mm of Hg pressure.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturethermometer and reflux condenser
  3. temperatureAfter this time the reaction mixture was cooled to room temperature
  4. filtrationwas filtered
  5. distillationThe filtrate was then distilled under vacuum

Sources & evidence

ORD record
ord-a660475f64ee4e8ea46eb2602cc4b81d
Source dataset
uspto-grants-1976_09
Patent number
US03983174

Reaction notes

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