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

HRID 443339Notes

Reaction equation

HRID 443339 reaction equation
C[N:2](C)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5]C=1.Br[CH:11]([CH3:15])[C:12](=[O:14])[CH3:13].[C:16](=O)(O)[O-].[Na+].[CH2:21](O)[CH3:22]>ClCCl>[CH3:16][C:8]1[CH:7]=[CH:6][CH:5]=[C:21]([CH3:22])[C:3]=1[NH:2][CH:11]([CH3:15])[C:12](=[O:14])[CH3:13]

Participants

6

Reactant 4

HCID 702EthanolHCID 949N,N-DimethylanilineHCID 131422-Butanone, 3-bromo-HCID 516892Sodium Bicarbonate

Product 1

HCID 124914753-(2,6-Dimethylphenylamino)-2-butanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 121 g (1 mol) dimethylaniline, 149 g (1 mol) 3-bromo-2-butanone and 126 g (1.5 mol) sodium bicarbonate in 500 ml ethanol was stirred at 60°-70° C. for about 18 hours. The reaction mixture was filtered and the filtrate evaporated under reduced pressure to give an oil. The oil was taken up in dichloromethane, dried over magnesium sulfate, treated with silica, filtered and evaporated under reduced pressure to give 174.8 g of 3-(2,6-dimethylphenylamino)-2-butanone as a light amber oil. The infrared spectrum of the product showed strong carbonyl absorption at 5.8 microns.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate evaporated under reduced pressure
  3. customto give an oil
  4. dry with materialdried over magnesium sulfate
  5. additiontreated with silica
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-01aeab78e9d349d28e302a2f02cbad62
Source dataset
uspto-grants-1981_04
Patent number
US04260410

Reaction notes

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