Methyl iodide → 1-(4-Methoxy-2,5-dimethylphenyl)ethanone

HRID 628526Notes

Reaction equation

HRID 628526 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5]([CH3:9])=[CH:4][C:3]=1[C:10](=[O:12])[CH3:11].CI.[C:15](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:15][O:8][C:6]1[C:5]([CH3:9])=[CH:4][C:3]([C:10](=[O:12])[CH3:11])=[C:2]([CH3:1])[CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2999742',5'-Dimethyl-4'-hydroxyacetophenone

Product 1

HCID 149071491-(4-Methoxy-2,5-dimethylphenyl)ethanoneYield 95.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1-(2,5-dimethyl-4-hydroxy-phenyl)-ethanone 14.6 g, methyl iodide 16.6 g, potassium carbonate 26.8 g and acetone 200 ml was stirred with heating under reflux for eight hours. The reaction mixture was cooled to room temperature and was filtered, and was then concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to give 1-(4-methoxy-2,5-dimethyl-phenyl)-ethanone 15.1 g.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for eight hours
  3. filtrationwas filtered
  4. concentrationwas then concentrated under reduced pressure

Sources & evidence

ORD record
ord-123b5862a84a42dc93b6af949b510a2f
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

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