Sodium Hydroxide → HCID 21569669, compound

HRID 1579849Notes

Reaction equation

HRID 1579849 reaction equation
[CH2:1]([O:3][C:4]1[CH2:8][CH2:7][C:6](=[O:9])[C:5]=1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18]CC)=[O:17])[CH3:2].[OH-].[Na+]>C(O)C>[CH2:1]([O:3][C:4]1[CH2:8][CH2:7][C:6](=[O:9])[C:5]=1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21569671HCID 21569671, compound

Product 1

HCID 21569669HCID 21569669, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture containing 22.16 parts of ethyl 2-ethoxy-5-oxocyclopent 1-eneheptanoate, 785 parts of 0.1N aqueous sodium hydroxide and 320 parts of ethanol is stored at room temperature for about 48 hours, then is concentrated to approximately 2/3 volume by distillation under reduced pressure. The residual solution is washed with ether, acidified with dilute hydrochloric acid, then extracted with ethyl acetate. The ethyl acetate extracts are washed with water, dried over anhydrous magnesium sulfate and evaporated to dryness by distillation under reduced pressure. The residual solid residue is purified by recrystallization from ether-benzene to afford 2-ethoxy-5-oxocyclopent-1-eneheptanoic acid, melting at about 65°-66°.

Workup

  1. concentrationis concentrated to approximately 2/3 volume by distillation under reduced pressure
  2. washThe residual solution is washed with ether
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate extracts are washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated to dryness by distillation under reduced pressure
  7. customThe residual solid residue is purified by recrystallization from ether-benzene

Sources & evidence

ORD record
ord-200d7c0a933e44f7959e1bed07694867
Source dataset
uspto-grants-1976_01
Patent number
US03931411

Reaction notes

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