Water → (4-(2,3-Dihydroxypropoxy)phenyl)(phenyl)methanone

HRID 931689

반응식

HRID 931689 반응식
[C:1]([C:9]1[CH:19]=[CH:18][C:12]([O:13][CH2:14][CH:15]2[CH2:17][O:16]2)=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.Cl(O)(=O)(=O)=[O:22].FC(F)(F)C(O)=O>ClCCCl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[C:1]([C:9]1[CH:19]=[CH:18][C:12]([O:13][CH2:14][CH:15]([OH:22])[CH2:17][OH:16])=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

8

반응물 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 24247Perchloric AcidHCID 3528162-[(4-Benzoylphenoxy)methyl]oxirane

생성물 1

HCID 58434142(4-(2,3-Dihydroxypropoxy)phenyl)(phenyl)methanone수율 66%

시약·촉매·용매 3

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 111,2-Dichloroethane용매HCID 6344Dichloromethane용매

반응 조건

온도
70 °C

실험 절차

2-(4-benzoylphenoxymethyl)oxirane (10.0 g; 39.3 mmol) was dissolved in 1,2-dichloroethane (100 mL). To the solution was charged water (100 mL), 1 M aqueous perchloric acid (25 mL), trifluoroacetic acid (5 mL) and tetrabutylammonium hydrogensulfate (1.336 g; 3.93 mmol). The biphasic reaction mixture was stirred vigorously and heated to 70° C. for 6 h. The reaction was cooled to ambient temperature, diluted with dichloromethane (100 mL) and the organic phase was separated. The aqueous phase was further extracted with dichloromethane (50 mL). The solvent were evaporated to give a white solid. Recrystallisation from 1,2-dimethoxyethane/isopropylalcohol provided the desired 3-(4-benzoylphenoxyl)propane-1,2-diol as a white solid (7.05 g; 66% yield).

후처리

  1. customThe biphasic reaction mixture
  2. temperatureThe reaction was cooled to ambient temperature
  3. customthe organic phase was separated
  4. extractionThe aqueous phase was further extracted with dichloromethane (50 mL)
  5. customThe solvent were evaporated
  6. customto give a white solid
  7. customRecrystallisation from 1,2-dimethoxyethane/isopropylalcohol

출처 및 근거

ORD 기록
ord-27f6d6197ae24333b16aa3d5140ad53f
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296835B2

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