Sodium Bicarbonate → HCID 20430688, compound

HRID 2413207Notes

Reaction equation

HRID 2413207 reaction equation
[C:1]1([C:6]2([CH2:11][OH:12])[CH2:10][CH:9]=[CH:8]O2)[CH2:5][CH2:4][CH2:3][CH:2]=1.C(=O)([O-])[OH:14].[Na+]>CC(C)=O.O>[OH:14][CH:10]1[CH:9]=[CH:8][C:11](=[O:12])[CH:6]1[CH:1]1[CH2:5][CH2:4][CH:3]=[CH:2]1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 70488488HCID 70488488, compound

Product 1

HCID 20430688HCID 20430688, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

2-Cyclopentenyl-2-furyl methanol (131 g, 0.8 mole) was dissolved in a 2:1 mixture (1.5 liters) of acetone and water in a reactor, and polyphosphoric acid (20 g) was added thereto. Thereafter, reaction was carried out at 50° to 60° C. for about 24 hours with stirring. After completion of the reaction, the reaction solution was cooled and neutralized with addition of a saturated aqueous solution (200 ml) of sodium hydrogen carbonate, followed by extraction with a solvent. The extract was washed with water, dried and concentrated. The residue obtained was distilled under reduced pressure to obtain 72 g (yield, 55%) of pure (±)-3-hydroxy-2-(2-cyclopentenyl)-4-cyclopenten-1-one having a boiling point of 115°-120° C./3 mmHg.

Workup

  1. customThereafter, reaction
  2. customAfter completion of the reaction
  3. temperaturethe reaction solution was cooled
  4. extractionfollowed by extraction with a solvent
  5. washThe extract was washed with water
  6. customdried
  7. concentrationconcentrated
  8. customThe residue obtained
  9. distillationwas distilled under reduced pressure

Sources & evidence

ORD record
ord-e7a41dd057f74426b25bf6726f847bfe
Source dataset
uspto-grants-1985_01
Patent number
US04496586

Reaction notes

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