Acetovanillone → Ethyl (4-acetyl-2-methoxyphenoxy)acetate

HRID 369878Notes

Reaction equation

HRID 369878 reaction equation
CN(C)C=O.[CH3:6][O:7][C:8]1[CH:13]=[C:12]([C:14](=[O:16])[CH3:15])[CH:11]=[CH:10][C:9]=1[OH:17].Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].C(=O)([O-])[O-].[K+].[K+]>O>[CH3:6][O:7][C:8]1[CH:13]=[C:12]([C:14](=[O:16])[CH3:15])[CH:11]=[CH:10][C:9]=1[O:17][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]

Participants

6

Reactant 4

HCID 2214AcetovanilloneHCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

Product 1

HCID 23282600Ethyl (4-acetyl-2-methoxyphenoxy)acetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To dimethylformamide (200 ml) are added 2-methoxy-4-acetylphenol (20 g), ethyl α-bromoacetate (15 ml) and potassium carbonate (18.3 g), and the mixture is stirred at room temperature overnight. After the reaction is complete, water is added to the mixture, and the mixture is extracted with ethyl acetate. The extract is washed with aqueous sodium hydrogen carbonate solution, and dried over magnesium sulfate, and concentrated under reduced pressure to remove the solvent. The resulting crystals are collected, and washed with n-hexane-diethyl ether to give ethyl α-(2-methoxy-4-acetylphenoxy)acetate (23.86 g).

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washThe extract is washed with aqueous sodium hydrogen carbonate solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto remove the solvent
  6. customThe resulting crystals are collected
  7. washwashed with n-hexane-diethyl ether

Sources & evidence

ORD record
ord-19a46f397f50424093ccc89a1b6dd616
Source dataset
uspto-grants-2000_10
Patent number
US06140330

Reaction notes

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