Benzyl Chloride → Hexaethylene Glycol Monobenzyl Ether
Reaction equation
[OH-].[Na+].[CH2:3]([OH:21])[CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][OH:20].[CH2:22](Cl)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O.[Cl-].[Na+].O>[CH2:22]([O:20][CH2:19][CH2:18][O:17][CH2:16][CH2:15][O:14][CH2:13][CH2:12][O:11][CH2:10][CH2:9][O:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][OH:21])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
An aqueous sodium hydroxide solution prepared by dissolving 3.99 g (100 mmol) NaOH in 4 ml water was added slowly to monodispersed hexaethylene glycol (28.175 g, 25 ml, 100 mmol). Benzyl chloride (3.9 g, 30.8 mmol, 3.54 ml) was added and the reaction mixture was heated with stirring to 100° C. for 18 hours. The reaction mixture was then cooled, diluted with brine (250 ml) and extracted with methylene chloride (200 ml×2). The combined organic layers were washed with brine once, dried over Na2SO4, filtered and concentrated in vacuo to a dark brown oil. The crude product mixture was purified via flash chromatography (silica gel, gradient elution: ethyl acetate to 9/1 ethyl acetate/methanol) to yield 8.099 g (70%) of monodispersed compound 1 as a yellow oil.
Workup
- temperaturethe reaction mixture was heated
- temperatureThe reaction mixture was then cooled
- extractionextracted with methylene chloride (200 ml×2)
- washThe combined organic layers were washed with brine once
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo to a dark brown oil
- customThe crude product mixture was purified via flash chromatography (silica gel, gradient elution: ethyl acetate to 9/1 ethyl acetate/methanol)
Sources & evidence
- ORD record
- ord-516e073a0db541218ca8bc0740e14034
- Source dataset
- uspto-grants-2007_01
- Patent number
- US07166571B2
Reaction notes
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