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

HRID 37053

Reaction equation

HRID 37053 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. Yield 39.5 g (49%) b.p. 65°-66° C. (0.055 mmHg).

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-923b1537a8f547878e110fc8e786586e
Source dataset
uspto-grants-1995_05
Patent number
US05419893

Linked notes

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