Water → HCID 23114221, compound

HRID 1787127Notes

Reaction equation

HRID 1787127 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:9].[C:10](=O)([O-])[O-].[K+].[K+].Br[C:17]([CH3:28])([CH3:27])[C:18]([C:20]1[CH:25]=[CH:24][C:23](Br)=[CH:22][CH:21]=1)=[O:19].O>CS(C)=O>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[O:9][C:17]([CH3:28])([CH3:27])[C:18]([C:20]1[CH:25]=[CH:24][C:23]([CH3:10])=[CH:22][CH:21]=1)=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 106872,3-DimethylphenolHCID 11430Potassium CarbonateHCID 23114064HCID 23114064, compound

Product 1

HCID 23114221HCID 23114221, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
35 °C

Procedure

To a mixture of 2,3-dimethylphenol (12.2 g, 100 mmol) and potassium carbonate (27.4 g, 200 mmol) in dimethylsulfoxide (138 mL) was added 2-bromo-1-(4-bromophenyl)-2-methylpropane-1-one (42.2 g, 175 mmol) at room temperature, and the mixture was warmed to 35° C. The mixture was stirred at the same temperature for 24 hours, poured into cold water (300 mL), and then extracted with diethyl ether. The organic layer was washed with a 4 N aqueous sodium hydroxide solution and a saturated brine, and then was dried over sodium sulfate. The solvent was concentrated under reduced pressure, and then was purified by silica gel column chromatography (ethyl acetate:hexane=1:9) to obtain 2-(2,3-dimethylphenoxy)-2-methyl-1-(4-methylphenyl)propane-1-one of oily matter. The obtained oily matter was dissolved in methanol (200 mL), sodium borohydride (3.8 g, 100 mmol) was added thereto at 0° C., and the mixture was warmed to room temperature. The oily matter was stirred at the same temperature for 1 hour, cooled to 0° C., and neutralized with 1 N hydrochloric acid, and then the solvent was distilled off under reduced pressure. The residue was extracted with ethyl acetate, and the extract solution was washed with a saturated brine, and then was dried over sodium sulfate. The solvent was distilled off under reduced pressure to obtain 17.1 g (yield 60%) of the title compound as an oily matter.

Workup

  1. extractionextracted with diethyl ether
  2. washThe organic layer was washed with a 4 N aqueous sodium hydroxide solution
  3. dry with materiala saturated brine, and then was dried over sodium sulfate
  4. concentrationThe solvent was concentrated under reduced pressure
  5. customwas purified by silica gel column chromatography (ethyl acetate:hexane=1:9)

Sources & evidence

ORD record
ord-89feb5e31fa848e9b03e5b269edaf633
Source dataset
uspto-grants-2009_03
Patent number
US07507841B2

Reaction notes

Loading…