Water → 2-(3,4,5-Trimethylphenoxy)-1-(4-isopropylphenyl)ethanone

HRID 1787149Notes

Reaction equation

HRID 1787149 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:13])[CH3:12])=[CH:7][CH:6]=1)=[O:4].[CH3:14][C:15]1[CH:16]=[C:17]([OH:23])[CH:18]=[C:19]([CH3:22])[C:20]=1[CH3:21].C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[CH3:14][C:15]1[CH:16]=[C:17]([CH:18]=[C:19]([CH3:22])[C:20]=1[CH3:21])[O:23][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:13])[CH3:12])=[CH:7][CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 106963,4,5-TrimethylphenolHCID 11430Potassium CarbonateHCID 140427562-Bromo-1-(4-(propan-2-yl)phenyl)ethan-1-one

Product 1

HCID 231138782-(3,4,5-Trimethylphenoxy)-1-(4-isopropylphenyl)ethanoneYield 96%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Bromo-1-(4-isopropylphenyl)ethanone obtained in Reference Example 164 (20 g, 82.9 mmol) and 3,4,5-trimethylphenol (10.3 g, 75.4 mmol) were added to a solution of potassium carbonate (12.5 g, 90.5 mmol) in acetonitrile solution (200 mL), and mixture was stirred with heating under reflux for 6 hours. The reaction solution was ice-cooled, was poured into cold water, which was extracted with ethyl acetate. The extract was washed with a saturated brine, and then was dried over sodium sulfate. Then, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:10). The obtained oily matter was crystallized from hexane-ethyl acetate to obtain 21.5 g (yield 96%) of the title compound. Melting point: 96-98° C.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 6 hours
  3. temperaturecooled
  4. extractionwas extracted with ethyl acetate
  5. washThe extract was washed with a saturated brine
  6. dry with materialwas dried over sodium sulfate
  7. distillationThen, the solvent was distilled off under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:10)
  9. customThe obtained oily matter was crystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-279fd297f5b14a1c98382efa4fddb87e
Source dataset
uspto-grants-2009_03
Patent number
US07507841B2

Reaction notes

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