Bromoacetic Acid → Benzyl 2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)acetate

HRID 1772309Notes

Reaction equation

HRID 1772309 reaction equation
[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][OH:10].[H-].[Na+].Br[CH2:14][C:15]([OH:17])=[O:16].Br[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C>[CH2:19]([O:17][C:15](=[O:16])[CH2:14][O:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][OH:10])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 6227Bromoacetic AcidHCID 7498Benzyl BromideHCID 8172Triethylene GlycolHCID 24758Sodium hydride

Product 1

HCID 58409191Benzyl 2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)acetateYield 15.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2-[2-(2-Hydroxy-ethoxy)-ethoxy]-ethanol (612 g, 414 mmol) was dissolved under argon in 875 mL of abs. DMF and cooled to 0° C. NaH (12.1 g, 277 mmol, 55% in mineral oil) was carefully added, the ice bath removed, and stirring continued for 1 h 80° C. The reaction mixture was cooled to ambient temperature and treated with bromoacetic acid (18.98 g, 137 mmol) which was added via dropping funnel as a DMF-solution (20 mL). After an additional 30 min. at 75° C., bromomethyl-benzene (23.36 g, 137 mmol) was added neat and esterification allowed to proceed for 30 min. Cooling, careful pouring onto crushed ice, extraction with ethyl acetate, washing with water, drying over Na2SO4, and evaporation of all solvents, followed by flash chromatography (SiO2, ethyl acetate/heptane=8/2) yielded 6.41 g of the title compound as a yellow oil, MS (ISP): 299.2 [M+H]+.

Workup

  1. customthe ice bath removed
  2. additionwas added
  3. waitAfter an additional 30 min. at 75° C.
  4. waitto proceed for 30 min
  5. temperatureCooling
  6. additioncareful pouring
  7. customonto crushed
  8. extractionice, extraction with ethyl acetate
  9. washwashing with water
  10. dry with materialdrying over Na2SO4, and evaporation of all solvents

Sources & evidence

ORD record
ord-97ad4214f3304ca9be72cddf23067e1d
Source dataset
uspto-grants-2016_02
Patent number
US09249179B2

Reaction notes

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