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

HRID 931689

Reaktionsgleichung

Reaktionsgleichung von HRID 931689
[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

Komponenten

8

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 111,2-DichloroethaneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-27f6d6197ae24333b16aa3d5140ad53f
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296835B2

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