Benzyl Bromide → Hexaethylene Glycol Monobenzyl Ether

HRID 1351025Notes

Reaction equation

HRID 1351025 reaction equation
[H-].[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](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O1CCCC1.O>[C:23]1([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])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 17472Hexaethylene GlycolHCID 24758Sodium hydride

Product 1

HCID 11164646Hexaethylene Glycol Monobenzyl EtherYield 56.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of sodium hydride (50% dispersion in mineral oil, 2.55 g) in tetrahydrofuran (100 mL) was added hexaethylene glycol (25 g). The reaction mixture was stirred at 5–15° C. for 10 minutes, then benzyl bromide (16.66 g) was added. The suspension was allowed to stand at 20° C. for 72 hours then the reaction mixture was diluted with water (250 mL) and extracted with cyclohexane (250+125 mL). Aqueous sodium chloride solution (15% w/w, 300 mL) was added to the aqueous phase and the resulting solution was extracted with ethyl acetate (3×250 mL). The combined ethyl acetate extracts were concentrated in vacuo to give the title compound as an orange oil (18.68 g). LC retention time 2.50 mins. Mass spectrum m/z 390 [MNH4+]

Workup

  1. waitto stand at 20° C. for 72 hours
  2. extractionextracted with cyclohexane (250+125 mL)
  3. additionAqueous sodium chloride solution (15% w/w, 300 mL) was added to the aqueous phase
  4. extractionthe resulting solution was extracted with ethyl acetate (3×250 mL)
  5. concentrationThe combined ethyl acetate extracts were concentrated in vacuo

Sources & evidence

ORD record
ord-944f80330fb347e4a90db481cc59c74a
Source dataset
uspto-grants-2007_05
Patent number
US07217409B2

Reaction notes

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