Ethylene Glycol → HCID 10536021, compound

HRID 1492313Notes

Reaction equation

HRID 1492313 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[CH2:12](O)[CH2:13][OH:14].C(OCC)(OCC)OCC>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:10]([O:9][C:7]([CH:3]1[CH2:4][CH2:5][CH2:6][C:2]21[O:14][CH2:13][CH2:12][O:1]2)=[O:8])[CH3:11]

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 31214Ethyl orthoformateHCID 69136Ethyl 2-oxocyclopentanecarboxylate

Product 1

HCID 10536021HCID 10536021, compoundYield 128.1%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

A mixture of ethyl 2-oxocyclopentanecarboxylate (Aldrich, 10.0 g, 64.0 mmol), ethylene glycol (18 mL, 323 mmol), triethyl orthoformate (21 mL, 126 mmol) and p-toluenesulfonic acid monohydrate (0.61 g, 3.21 mmol) in toluene (150 mL) was heated under reflux with removing distillate with a Dean-Stark apparatus for 1 h. The mixture was cooled and poured into NaHCO3 solution, and the organic layer was separated. The aqueous layer was extracted with diethyl ether, and the combined organic layers were washed with NaCl solution and dried over Na2SO4. Filtration and concentration gave 16.41 g of 2, as a pale yellow oil, which was used in the next reaction without further purification.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. customwith removing distillate with a Dean-Stark apparatus for 1 h
  4. temperatureThe mixture was cooled
  5. additionpoured into NaHCO3 solution
  6. customthe organic layer was separated
  7. extractionThe aqueous layer was extracted with diethyl ether
  8. washthe combined organic layers were washed with NaCl solution
  9. dry with materialdried over Na2SO4
  10. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-4ba803fbb3f04821a48f4e3999b6a6d3
Source dataset
uspto-grants-1994_12
Patent number
US05373004

Reaction notes

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