1,2-Dichloroethane → 1,1'-Dimethyl 2,2'-oxybis(acetate)

HRID 1614519

Reaction equation

HRID 1614519 reaction equation
[C:1]([OH:9])(=[O:8])[CH2:2][O:3][CH2:4][C:5]([OH:7])=O.[CH3:10][OH:11].Cl[CH2:13]CCl>>[CH3:10][O:11][C:5](=[O:7])[CH2:4][O:3][CH2:2][C:1]([O:9][CH3:13])=[O:8]

Participants

4

Reactant 3

HCID 111,2-DichloroethaneHCID 887MethanolHCID 8088Diglycolic Acid

Product 1

HCID 2018771,1'-Dimethyl 2,2'-oxybis(acetate)

Procedure

Diglycolic acid (67.05 g, 0.5 mol) was dissolved in a mixture of methanol (122 ml, 30 mol) and 1,2-dichloroethane (150 ml). KSF-catalyst (Aldrich) (2.5 g) was added and the mixture was refluxed for 15 hours. The mixture was cooled to ambient temperature, filtered through alumina, washed with aqueous saturated sodium hydrogen carbonate (100 ml) and dried over magnesium sulphate. The solvent was evaporated and diglycolic acid dimethyl ester was isolated after distillation as a colourless oil.

Workup

  1. additionKSF-catalyst (Aldrich) (2.5 g) was added
  2. temperaturethe mixture was refluxed for 15 hours
  3. filtrationfiltered through alumina
  4. washwashed with aqueous saturated sodium hydrogen carbonate (100 ml)
  5. dry with materialdried over magnesium sulphate
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-0511df2ffccf40bc98e811058e3432a5
Source dataset
uspto-grants-1993_03
Patent number
US05198208

Linked notes

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