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

HRID 2376336Notes

Reaction equation

HRID 2376336 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-6edf057d7c8444b6992717e3599a3ea1
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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