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

HRID 931689

反応式

HRID 931689 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 94433Tetrabutylammonium hydrogen sulfate触媒HCID 111,2-Dichloroethane溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
70 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-27f6d6197ae24333b16aa3d5140ad53f
出典データセット
uspto-grants-2016_03
特許番号
US09296835B2

関連ノート

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