Diketene → N-(3-Butylphenyl)-3-oxobutanamide

HRID 597451Notes

Reaction equation

HRID 597451 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[CH2:7]([C:11]1[CH:12]=[C:13]([CH:15]=[CH:16][CH:17]=1)[NH2:14])[CH2:8][CH2:9][CH3:10]>C1C=CC=CC=1>[CH2:7]([C:11]1[CH:12]=[C:13]([CH:15]=[CH:16][CH:17]=1)[NH:14][C:4](=[O:5])[CH2:3][C:2](=[O:6])[CH3:1])[CH2:8][CH2:9][CH3:10]

Participants

4

Reactant 2

HCID 12661DiketeneHCID 793333-Butylbenzenamine

Product 1

HCID 21445129N-(3-Butylphenyl)-3-oxobutanamideYield 78.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
30 °C

Procedure

3.9 g of diketene were added to a mixture of 6.9 g of m-(n-butyl)-aniline and 70 ml of benzene and the mixture was stirred for 2 hours at 30° C. The benzene was evaporated under reduced pressure and the residue was chromatographed over silica gel. Elution with an 8-2 mixture of methylene chloride and ethyl acetate yielded 8.5 g of m-(n-butyl)-acetylacetanilide in the form of an oil with a refractive index of nD 20 = 1.5355.

Workup

  1. customThe benzene was evaporated under reduced pressure
  2. customthe residue was chromatographed over silica gel
  3. washElution
  4. additionwith an 8-2 mixture of methylene chloride and ethyl acetate

Sources & evidence

ORD record
ord-eb57f4bede5e49ab9fe9c70183ddf173
Source dataset
uspto-grants-1977_03
Patent number
US04014679

Reaction notes

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