Sodium Acetate → 2-Methyl-4-oxo-3-(prop-2-en-1-yl)cyclopent-2-en-1-yl acetate

HRID 485120Notes

Reaction equation

HRID 485120 reaction equation
C(O[C:5]1([CH3:14])[CH:9]=[CH:8][C:7](=[O:10])[CH:6]1[CH2:11][CH:12]=[CH2:13])(=O)C.[C:15]([O-:18])(=[O:17])[CH3:16].[Na+]>C(O)(=O)C>[C:15]([O:18][CH:9]1[CH2:8][C:7](=[O:10])[C:6]([CH2:11][CH:12]=[CH2:13])=[C:5]1[CH3:14])(=[O:17])[CH3:16]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 13335393HCID 13335393, compound

Product 1

HCID 131027602-Methyl-4-oxo-3-(prop-2-en-1-yl)cyclopent-2-en-1-yl acetateYield 176.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

Into a four necked flask equipped with an agitator and a thermometer, 3-acetoxy-2-allyl-3-methyl-4-cyclopentenone (19.4 g), acetic acid (80 ml) and sodium acetate (4 g) were charged and refluxed for 5 hours with agitation. After the completion of the reaction, acetic acid was evaporated off under reduced pressure. The residue was shaken with toluene (70 ml) and water (40 ml). The organic layer was separated, washed with an aqueous solution of sodium bicarbonate and then water and concentrated. The residue was distilled to obtain 4-acetoxy-2-allyl-3-methyl-2-cyclopentenone (16.7 g). Yield, 86%. B.P., 100°-110° C./0.1-0.3 mmHg.

Workup

  1. customInto a four necked flask equipped with an agitator
  2. temperaturerefluxed for 5 hours with agitation
  3. customwas evaporated off under reduced pressure
  4. customThe organic layer was separated
  5. washwashed with an aqueous solution of sodium bicarbonate
  6. concentrationwater and concentrated
  7. distillationThe residue was distilled

Sources & evidence

ORD record
ord-83a2d24f388e4c3ea1585f823b98d8f1
Source dataset
uspto-grants-1985_08
Patent number
US04535182

Reaction notes

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