Bromomethyl 4-methoxyphenyl ketone → HCID 18784184, compound

HRID 1108764Notes

Reaction equation

HRID 1108764 reaction equation
[CH3:1][C:2](C)([O-:4])[CH3:3].[K+].[C:7]([O:13][CH2:14][CH3:15])(=[O:12])[CH2:8]C(C)=O.[CH3:16][O:17][C:18]1[CH:27]=[CH:26][C:21]([C:22](=[O:25])[CH2:23]Br)=[CH:20][CH:19]=1>C1C=CC=CC=1>[CH3:16][O:17][C:18]1[CH:27]=[CH:26][C:21]([C:22](=[O:25])[CH2:23][CH:8]([CH2:1][C:2](=[O:4])[CH3:3])[C:7]([O:13][CH2:14][CH3:15])=[O:12])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 8868Ethyl AcetoacetateHCID 23665647Potassium tert-butoxide

Product 1

HCID 18784184HCID 18784184, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

After adding potassium tert-butoxide to a solution of ethyl acetoacetate (25.7 g) in benzene (420 ml) while cooling on ice, 4-methoxyphenacyl bromide (24.8 g) was gradually added and the mixture was refluxed for an hour. After allowing the reaction solution to cool, it was washed with 5% sodium hydroxide and purified water, and dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to give 26.2 g of ethyl 2-[2-(4-methoxyphenyl)-2-oxoethyl]-4-oxopentanoate (87.0% yield).

Workup

  1. additionwas gradually added
  2. temperaturethe mixture was refluxed for an hour
  3. temperatureto cool
  4. washit was washed with 5% sodium hydroxide
  5. custompurified water
  6. dry with materialdried with anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-cd529ceff3754de6a072eea152387e45
Source dataset
uspto-grants-2000_05
Patent number
US06069176

Reaction notes

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