Ethylene Glycol → 2-(Diphenylmethoxy)ethan-1-ol

HRID 1297038Notes

Reaction equation

C1(C)C=CC=CC=1.[CH2:8]([OH:11])[CH2:9][OH:10].[CH:12](O)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>S(=O)(=O)(O)O.CCOCC>[CH:12]([O:10][CH2:9][CH2:8][OH:11])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 90 °C

Procedure

8 ml of toluene and 2 drops of concentrated sulfuric acid were added to 621 mg (10.0 mmol) of ethylene glycol, and they were heated to 90° C. 737 mg (4.0 mmol) of benzhydrol was added dropwise to the obtained mixture for the duration of 50 minutes. 30 minutes after, 621 mg (10.0 mmol) of ethylene glycol was added thereto and they were stirred under heating for 40 minutes. Ether was added to the reaction mixture, and the organic layer was successively washed with water, saturated aqueous sodium hydrogencarbonate solution, water and finally saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate=2/1) to obtain the title compound.

Workup

temperatureunder heating for 40 minutes
washthe organic layer was successively washed with water, saturated aqueous sodium hydrogencarbonate solution, water and finally saturated aqueous sodium chloride solution
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record: ord-f8b9ee9845f146048f475e232bb9494f
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07247645B2

Reaction notes

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