Water → HCID 23114221, 화합물

HRID 2376309노트

반응식

HRID 2376309 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 23114221HCID 23114221, 화합물

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
35 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-6157429e0b4f4f7c89fd2f2055cfad4a
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07465815B2

반응 노트

불러오는 중…