2,6-Dimethylaniline → HCID 21412829, compound

HRID 1576939Notes

Reaction equation

HRID 1576939 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH2:4].Br[CH2:11][CH:12]=[O:13].C(=O)([O-])[O-].[Na+].[Na+]>>[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH:4][CH2:11][CH:12]=[O:13]

Participants

4

Reactant 3

HCID 68962,6-DimethylanilineHCID 10340Sodium CarbonateHCID 105131Acetaldehyde, bromo-

Product 1

HCID 21412829HCID 21412829, compound

Conditions

Temperature
150 °C

Procedure

2,6-Dimethylaniline (100 grams), the dihexyl acetal of 2-bromoacetaldehyde (70 grams) and sodium carbonate (32 grams) are charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The mixture is heated at a temperature of about 150°C for a period of about 30 hours. After this time the reaction mixture is cooled to room temperature and is filtered. The filtrate is then distilled under vacuum to yield the desired product the dihexyl acetal of 2-(2,6-dimethylanilino)acetaldehyde as the residue.

Workup

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

Sources & evidence

ORD record
ord-2dc072d084cd492aaecf9332578cde46
Source dataset
uspto-grants-1976_09
Patent number
US03983174

Reaction notes

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