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

HRID 931689Notes

Reaction equation

[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

Participants

Conditions

Temperature: 70 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-27f6d6197ae24333b16aa3d5140ad53f
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296835B2

Reaction notes

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