Diketene → m-Benzyloxy-acetylacetanilide

HRID 259059Notes

Reaction equation

HRID 259059 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[CH2:7]([O:14][C:15]1[CH:16]=[C:17]([CH:19]=[CH:20][CH:21]=1)[NH2:18])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1C=CC=CC=1>[CH2:7]([O:14][C:15]1[CH:16]=[C:17]([CH:19]=[CH:20][CH:21]=1)[NH:18][C:4](=[O:5])[CH2:3][C:2](=[O:6])[CH3:1])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 12661DiketeneHCID 928923-Benzyloxyaniline

Product 1

HCID 21422799m-Benzyloxy-acetylacetanilideYield 84.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
10 °C

Procedure

84 g of diketene were added over 30 minutes to a mixture of 200 g of m-benzyloxy-aniline [Morton, J. Biol. Chem., (1949), p. 259] in 1 liter of benzene cooled to 10°C. and after stirring the mixture for 6 hours, the benzene was distilled off under reduced pressure. The residue was added to isopropyl ether and the mixture was vacuum filtered. The recovered precipitate was washed with isopropyl ether and dried to obtain 240 g of m-benzyloxy-acetylacetanilide melting at 80°C.

Workup

  1. distillationthe benzene was distilled off under reduced pressure
  2. additionThe residue was added to isopropyl ether
  3. filtrationfiltered
  4. washThe recovered precipitate was washed with isopropyl ether
  5. customdried

Sources & evidence

ORD record
ord-51332adcc6e2463c90fc45704a2908e9
Source dataset
uspto-grants-1977_07
Patent number
US04036633

Reaction notes

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