Benzyl Bromide → Hexaethylene Glycol Monobenzyl Ether

HRID 1351032Notes

Reaction equation

[CH2:1]([OH:19])[CH2:2][O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][OH:18].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(OC(C)C)(C)C.[OH-].[Na+]>O.O1CCCC1>[C:21]1([CH2:20][O:18][CH2:17][CH2:16][O:15][CH2:14][CH2:13][O:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][O:6][CH2:5][CH2:4][O:3][CH2:2][CH2:1][OH:19])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 20 °C

Procedure

To a stirred mixture of hexaethylene glycol (10 g), benzyl bromide (4.53 mL) and diisopropyl ether (25 mL) was added tetrahydrofuran (10 mL). The mixture was cooled to 15–20° C. and aqueous sodium hydroxide (10.8M, 4.92 mL) was added slowly maintaining the temperature at 15–20° C. during addition. The resulting mixture was allowed to warm to 20° C. and stirred for a further 17 hours. Water (50 mL) was then added to the reaction mixture, which was then washed with diisopropyl ether (25 mL). Sodium chloride (10 g) was added to the aqueous phase which was extracted with ethyl acetate (3×25 mL). The combined ethyl acetate extracts were dried (Na2SO4) and concentrated in vacuo to give the title compound as a mobile oil (6.29 g). GC retention time 14.2 mins

Workup

temperatureThe mixture was cooled to 15–20° C.
temperaturemaintaining the temperature at 15–20° C.
additionduring addition
washwas then washed with diisopropyl ether (25 mL)
additionSodium chloride (10 g) was added to the aqueous phase which
extractionwas extracted with ethyl acetate (3×25 mL)
dry with materialThe combined ethyl acetate extracts were dried (Na2SO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-41755b19042d477c8867e0512e3b839f
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07217409B2

Reaction notes

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