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

HRID 485123Notes

Reaction equation

HRID 485123 reaction equation
[CH2:1]([CH:4]1[C:8](O)([CH3:9])[CH:7]=[CH:6][C:5]1=[O:11])[CH:2]=[CH2:3].[C:12]([O-:15])(=[O:14])[CH3:13].[Na+]>C(O)(=O)C>[C:12]([O:15][CH:7]1[CH2:6][C:5](=[O:11])[C:4]([CH2:1][CH:2]=[CH2:3])=[C:8]1[CH3:9])(=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 128798724-Hydroxy-4-methyl-5-(prop-2-en-1-yl)cyclopent-2-en-1-one

Product 1

HCID 131027602-Methyl-4-oxo-3-(prop-2-en-1-yl)cyclopent-2-en-1-yl acetateYield 390.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

In the same apparatus as in Example 1, 2-allyl-3-hydroxy-3-methyl-4-cyclopentenone (15.2 g), acetic acid (45 ml) and sodium acetate (2 g) were charged and heated to reflux for 7 hours. After the completion of the reaction, acetic acid was evaporated off under reduced pressure. The residue was extracted with toluene (60 ml) and water (40 ml) and treated as in Example 1 to obtain 4-acetoxy-2-allyl-3-methyl-2-cyclopentenone (18.5 g). Yield, 95.3%. B.P., 100°-110° C./0.1-0.3 mmHg.

Workup

  1. temperatureheated
  2. temperatureto reflux for 7 hours
  3. customwas evaporated off under reduced pressure
  4. extractionThe residue was extracted with toluene (60 ml) and water (40 ml)
  5. additiontreated as in Example 1

Sources & evidence

ORD record
ord-b15c076b8b4a46448ada65822b435708
Source dataset
uspto-grants-1985_08
Patent number
US04535182

Reaction notes

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