HCID 20389946, compound → 7-[4-(Acetyloxy)-5-oxocyclopent-1-en-1-yl]heptanoic acid

HRID 426776Notes

Reaction equation

HRID 426776 reaction equation
[O:1]1[CH:3]2[CH2:4][CH2:5][C:6](=O)[C:2]12[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15]>C(O)(=O)C>[C:14]([O:16][CH:4]1[C:3](=[O:1])[C:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:6][CH2:5]1)(=[O:15])[CH3:13]

Participants

3

Reactant 1

HCID 20389946HCID 20389946, compound

Product 1

HCID 203899457-[4-(Acetyloxy)-5-oxocyclopent-1-en-1-yl]heptanoic acidYield 78.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of (±)-7-(1,2-epoxy-5-oxocyclopentyl)-heptanoic acid (3.0 g) in glacial acetic acid (75 ml) was heated at reflux for 8 hours. The excess acetic acid was then removed in vacuo to give an oil which crystallised on standing. Recrystallisation from a mixture of water and ethanol gave (±)-7-(4-acetoxy-5-oxocyclopent-1-enyl)heptanoic acid (1.4 g), m.p. 62°-65° C.

Workup

  1. temperatureat reflux for 8 hours
  2. customThe excess acetic acid was then removed in vacuo
  3. customto give an oil which
  4. customcrystallised
  5. customRecrystallisation
  6. additionfrom a mixture of water and ethanol

Sources & evidence

ORD record
ord-54e1600e458f476da1c8692254b29250
Source dataset
uspto-grants-1979_10
Patent number
US04171375

Reaction notes

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