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

HRID 2071196Notes

Reaction equation

HRID 2071196 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 (120 grams), the diethyl acetal of 2-chloroacetaldehyde (78.8 grams) and sodium carbonate (42.4 grams) were charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture was heated at 150° C. for a period of about 30 hours. After this time the mixture was filtered and the filtrate was distilled to yield the desired product the diethyl acetal of 2-(2,6-diethylanilino)acetaldehyde having a boiling point of 130° C. at 1 mm of Hg pressure.

Workup

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

Sources & evidence

ORD record
ord-98cda60feefd4d609fc6cae681890b14
Source dataset
uspto-grants-1977_09
Patent number
US04046554

Reaction notes

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