Benzyl Chloride → Hexaethylene Glycol Monobenzyl Ether

HRID 895093Notes

Reaction equation

HRID 895093 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]=1

Participants

6

Reactant 3

HCID 7503Benzyl ChlorideHCID 14798Sodium Hydroxide2×HCID 17472Hexaethylene Glycol

Product 1

HCID 11164646Hexaethylene Glycol Monobenzyl Ether

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 57417360Sodium chloride; waterSolvent

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.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureThe reaction mixture was then cooled
  3. extractionextracted with methylene chloride (200 ml×2)
  4. washThe combined organic layers were washed with brine once
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo to a dark brown oil

Sources & evidence

ORD record
ord-001087fb430345a48209c14678b9183c
Source dataset
uspto-grants-2005_07
Patent number
US06913903B2

Reaction notes

Loading…