Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethylene Glycol | HCID 174 | — |
| Reactant | Boron trifluoride etherate | HCID 8000 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Dimethyl 4-oxocyclopentane-1,2-dicarboxylate | HCID 4083807 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 68140428 | HCID 68140428 | 89.7% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US03983152 |
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| Source dataset | uspto-grants-1976_09 |
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| ORD ID | ord-d67b7400a6474f35837b540eda64ef39 |
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| Source note | uspto-grants-1976_09 |
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