Ethylene Glycol → HCID 68140428, compound

HRID 1576892Notes

Reaction equation

HRID 1576892 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH:9]([C:10]([O:12][CH3:13])=[O:11])[CH2:8][C:7](=[O:14])[CH2:6]1)=[O:4].[CH2:15](O)[CH2:16][OH:17].B(F)(F)F.CCOCC.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:15]1[CH2:16][O:17][CH:6]2[CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH:9]([C:10]([O:12][CH3:13])=[O:11])[CH2:8][CH:7]2[O:14]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 8000Boron trifluoride etherate2×HCID 516892Sodium BicarbonateHCID 4083807Dimethyl 4-oxocyclopentane-1,2-dicarboxylate

Product 1

HCID 68140428HCID 68140428, compoundYield 89.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 250 ml of dichloromethane were dissolved 124 g of 3,4-dimethoxycarbonylcyclopentanone and 155 g of ethylene glycol and to the solution was added dropwise 94 g of boron trifluoride ethyl etherate at 0° - 5°C. After completion of the addition, the reaction mixture was stirred for 2 hours at 10° - 16°C and next for 1.5 hours at 16° - 23°C. After completion of the reaction, the reaction mixture was added dropwise to 1.5l of a saturated aqueous sodium bicarbonate containing pieces of ice in order to decompose the excess of the boron trifluoride etherate. The mixture was extracted three times with 1 l of ether. The extract was washed with a saturated aqueous sodium chloride and a saturated aqueous sodium bicarbonate and dried over anhydrous sodium sulfate. The solvent was distilled off from the extract to give 135.7 g of the desired product as colorless oil.

Workup

  1. additionAfter completion of the addition
  2. customAfter completion of the reaction
  3. extractionThe mixture was extracted three times with 1 l of ether
  4. washThe extract was washed with a saturated aqueous sodium chloride
  5. dry with materiala saturated aqueous sodium bicarbonate and dried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off from the
  7. extractionextract

Sources & evidence

ORD record
ord-d67b7400a6474f35837b540eda64ef39
Source dataset
uspto-grants-1976_09
Patent number
US03983152

Reaction notes

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