M-Cresol → alpha-(3-Methylphenoxy)acetophenone

HRID 1735705Notes

Reaction equation

HRID 1735705 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[CH:11]1[C:16]([OH:17])=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:18].C(=O)([O-])[O-].[K+].[K+]>[Cu].O>[CH3:18][C:12]1[CH:11]=[C:16]([CH:15]=[CH:14][CH:13]=1)[O:17][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4]

Participants

6

Reactant 3

HCID 342M-CresolHCID 107572-ChloroacetophenoneHCID 11430Potassium Carbonate

Product 1

HCID 14970243alpha-(3-Methylphenoxy)acetophenoneYield 92%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 50 g (0.324 mol) of 2-chloroacetophenone, 104.8 g (0.97 mol) of m-cresol, 45 g (0.326 mol) of potassium carbonate and 1 g of copper is heated at 120° C. for 16 hours. After cooling it is poured into water and extracted twice with methyl tert-butyl ether (MTB ether). The ether phase is washed five times with concentrated sodium hydroxide solution and then twice with water, dried and concentrated. 67.2 g (92% yield) of 2-(3-methylphenoxy)acetophenone remain as yellow oil.

Workup

  1. temperatureAfter cooling it
  2. extractionextracted twice with methyl tert-butyl ether (MTB ether)
  3. washThe ether phase is washed five times with concentrated sodium hydroxide solution
  4. dry with materialtwice with water, dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bcb894c352de43ba98309bae049c7496
Source dataset
uspto-grants-1996_07
Patent number
US05538940

Reaction notes

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