Water → 2-(4-Methylsulfanylbenzyl)phenol

HRID 554507노트

반응식

HRID 554507 반응식
CSC.C([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([S:25][CH3:26])=[CH:21][CH:20]=1)C1C=CC=CC=1.O>C(Cl)Cl>[CH3:26][S:25][C:22]1[CH:23]=[CH:24][C:19]([CH2:18][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[OH:11])=[CH:20][CH:21]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 1068Dimethyl SulfideHCID 674612941-Benzyloxy-(4-methylsulfanylbenzyl)benzene

생성물 1

HCID 674586422-(4-Methylsulfanylbenzyl)phenol수율 91%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

In a nitrogen stream, dimethylsulfide (7.25 mL, 138 mmol) and a boron trifluoride-diethyl ether complex (2.1 mL, 8.8 mmol) were added to a solution of 1-benzyloxy-(4-methylsulfanylbenzyl)benzene (1.9 g, 5.9 mmol) in methylene chloride (15 mL) under cooling with ice, and the reaction mixture was stirred for 48 hours while gradually raising its temperature to room temperature. Water was added thereto under cooling with ice and the mixture was extracted with methylene chloride. The organic layer was washed with a saturated sodium chloride aqueous solution and dried (anhydrous magnesium sulfate), and then the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:5)] to obtain the title compound (1.19 g, 91%).

후처리

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. extractionthe mixture was extracted with methylene chloride
  4. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  5. dry with materialdried (anhydrous magnesium sulfate)
  6. distillationthe solvent was distilled under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:5)]

출처 및 근거

ORD 기록
ord-d15715a9b1184917a01e35f32481ea0b
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08048897B2

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