Ethylene Glycol → 2-[2-(Methoxycarbonyl)ethyl]-2-phenyl-1,3-dioxolane

HRID 1607400

Reaction equation

HRID 1607400 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH2:4][CH2:5][C:6](=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH2:15](O)[CH2:16][OH:17].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:14])[CH2:4][CH2:5][C:6]1([O:17][CH2:16][CH2:15][O:13]1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 141190Benzenebutanoic acid, gamma-oxo-, methyl ester

Product 1

HCID 100371022-[2-(Methoxycarbonyl)ethyl]-2-phenyl-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 2.0 g of 3-benzoylpropionic acid methyl ester in 50 ml of dry benzene were added 0.7 ml of ethylene glycol and 0.01 g of anhydrous-p-toluene-sulfonic acid and the mixture was heated under reflux for 17 hours while removing water formed during the reaction by using a molecular sieve. After cooling, the reaction mixture was washed with a saturated sodium chloride aqueous solution, and concentrated under reduced pressure. The residue was purified by silica gel flash column chromatography (eluent: benzene/hexane=1/1 by volume) to obtain 1.8 g of 4,4-ethylenedioxy-4-phenylbutyric acid methyl ester.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 17 hours
  3. customwhile removing water
  4. customformed during the reaction
  5. temperatureAfter cooling
  6. washthe reaction mixture was washed with a saturated sodium chloride aqueous solution
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel flash column chromatography (eluent: benzene/hexane=1/1 by volume)

Sources & evidence

ORD record
ord-17cb79a884504a5682a49f850efe5a25
Source dataset
uspto-grants-1989_09
Patent number
US04863904

Linked notes

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