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

HRID 526277Notes

Reaction equation

HRID 526277 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 (62.2 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 at 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 crashed 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. extractionice, extraction with ethyl acetate
  8. washwashing with water
  9. dry with materialdrying over Na2SO4, and evaporation of all solvents

Sources & evidence

ORD record
ord-a90c63daf9204b6d8d6e381223673929
Source dataset
uspto-grants-2016_05
Patent number
US09345775B2

Reaction notes

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