Acetone → HCID 53891928, compound

HRID 542957Notes

Reaction equation

HRID 542957 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([OH:10])[C:7]([NH:11][C:12](=[O:14])[CH3:13])=[C:6]([OH:15])[CH:5]=1.[CH2:17](Br)[CH:18]=[CH2:19].C(=O)([O-])[O-].[K+].[K+].[CH3:27][C:28]([CH3:30])=O>>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:5]=[C:6]([O:15][CH2:17][CH:18]=[CH2:19])[C:7]([NH:11][C:12](=[O:14])[CH3:13])=[C:8]([O:10][CH2:30][CH:28]=[CH2:27])[CH:9]=1

Participants

5

Reactant 4

HCID 180AcetoneHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 53960010Methyl 4-acetamido-3,5-dihydroxybenzoate

Product 1

HCID 53891928HCID 53891928, compound

Procedure

A mixture of 11.25 g. of 4-acetamido-3,5-dihydroxy-benzoic acid methyl ester, 12.1 g. of allyl bromide, 15 g. of dry potassium carbonate and 100 ml. of acetone was boiled and stirred on a reflux condenser for 17 hours. The acetone was removed by distillation. The residue was taken up in water/ethyl acetate. Thereafter, the organic phase separated, washed with water, dried and evaporated. After recrystallization from ethyl acetate/petroleum ether, there was obtained 4-acetamido-3,5-diallyloxy-benzoic acid methyl ester having a melting point of 135°-137° C.

Workup

  1. additionA mixture of 11.25 g
  2. customThe acetone was removed by distillation
  3. customThereafter, the organic phase separated
  4. washwashed with water
  5. customdried
  6. customevaporated
  7. customAfter recrystallization from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-0b653d88d89b4fcbbc6455a4583e836a
Source dataset
uspto-grants-1987_04
Patent number
US04659818

Reaction notes

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