Ethylene Glycol → HCID 4305401, compound

HRID 1430222Notes

Reaction equation

HRID 1430222 reaction equation
[O:1]=[C:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH2:15](O)[CH2:16][OH:17].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[C:9]1([C:2]2([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])[O:17][CH2:16][CH2:15][O:1]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 7170Ethyl benzoylacetateHCID 516892Sodium Bicarbonate

Product 1

HCID 4305401HCID 4305401, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of ethyl 3-oxo-3-phenylpropanoate (23.74 g) in toluene, ethyleneglycol (23.04 g), and p-toluenesulfonic acid (200 mg) in toluene (300 mL) was stirred under reflux with a Dean-Stark trap for 15 hours. The cooled mixture was poured onto saturated aqueous sodium bicarbonate (100 mL) and the organic layer was washed with water, brine and dried over Na2SO4. Filtration and evaporation of solvent provided the title compound which was used in the next reaction without further purification.

Workup

  1. temperatureunder reflux with a Dean-Stark trap for 15 hours
  2. washthe organic layer was washed with water, brine
  3. dry with materialdried over Na2SO4
  4. filtrationFiltration and evaporation of solvent

Sources & evidence

ORD record
ord-96dbb94b2fba4f5c8577cd6be29208a5
Source dataset
uspto-grants-2015_01
Patent number
US08940737B2

Reaction notes

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