Sodium Bicarbonate → (+/-)-3-Hydroxy-2-(1-methyl-2-propynyl)-4-cyclopenten-1-one

HRID 2413205Notes

Reaction equation

HRID 2413205 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6](O)[CH:7]([CH3:10])[C:8]#[CH:9].C(=O)([O-])[OH:13].[Na+]>CC(C)=O.O>[OH:1][CH:5]1[CH:4]=[CH:3][C:2](=[O:13])[CH:6]1[CH:7]([CH3:10])[C:8]#[CH:9]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 133628502-(1-Hydroxy-2-methyl-3-butynyl)-furan

Product 1

HCID 13037840(+/-)-3-Hydroxy-2-(1-methyl-2-propynyl)-4-cyclopenten-1-oneYield 52%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

1-(2-Furyl)-2-methyl-3-butyn-1-ol (15 g, 0.1 mole) was dissolved in a 2:1 mixture (150 ml) of acetone and water in a reactor, and p-toluenesulfonic acid (3 g) was dried. Thereafter, reaction was carried out at 50° to 60° C. for about 48 hours with stirring. After completion of the reaction, the reaction solution was cooled and neutralized with addition of a saturated aqueous solution (30 ml) of sodium hydrogen carbonate, followed by extraction with a solvent. The extrect was washed with water, dried and concentrated. The residue obtained was distilled under reduced pressure to obtain 7.8 g (yield, 52%) of pure (±)-3-hydroxy-2-(1-methyl-2-propynyl)-4-cyclopenten-1-one having a boiling point of 110°-115° C./3 mmHg.

Workup

  1. dry with materialp-toluenesulfonic acid (3 g) was dried
  2. customThereafter, reaction
  3. customAfter completion of the reaction
  4. temperaturethe reaction solution was cooled
  5. extractionfollowed by extraction with a solvent
  6. washThe extrect was washed with water
  7. customdried
  8. concentrationconcentrated
  9. customThe residue obtained
  10. distillationwas distilled under reduced pressure

Sources & evidence

ORD record
ord-fdf6c05bef82402b8cb5de67f29b1954
Source dataset
uspto-grants-1985_01
Patent number
US04496586

Reaction notes

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