Ethylene Glycol → HCID 4305401, compound

HRID 1778831Notes

Reaction equation

HRID 1778831 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-4c3c8c36fdf6470386655b42cce1e52d
Source dataset
uspto-grants-2016_02
Patent number
US09266877B2

Reaction notes

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