Acetoin → 3-(2,6-Dimethylphenylamino)-2-butanone

HRID 46579

Reaction equation

HRID 46579 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH2:4].[OH:10][CH:11]([CH3:15])[C:12](=O)[CH3:13]>C1C=CC=CC=1>[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH:4][CH:12]([CH3:13])[C:11](=[O:10])[CH3:15]

Participants

4

Reactant 2

HCID 179AcetoinHCID 68962,6-Dimethylaniline

Product 1

HCID 124914753-(2,6-Dimethylphenylamino)-2-butanoneYield 94.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 484.8 g (4 mols) 2,6-dimethylaniline and 422.8 g (4.8 mols) 3-hydroxy-2-butanone in 1200 ml benzene was heated under reflux for 21 hours in a reaction vessel equipped with a Dean-Stark trap. The reaction mixture was then cooled, washed with four 600-ml portions of water, slurried with silica gel, filtered and evaporated under reduced pressure to give 722 g of 3-(2,6-dimethylphenylamino)-2-butanone, as an orange oil. The infrared spectrum of the product showed strong carbonyl absorption at 6.3 microns.

Workup

  1. temperatureunder reflux for 21 hours in a reaction vessel
  2. customequipped with a Dean-Stark trap
  3. temperatureThe reaction mixture was then cooled
  4. washwashed with four 600-ml portions of water
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b126410ed25f439aa70959958af44514
Source dataset
uspto-grants-1979_11
Patent number
US04174210

Linked notes

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