Water → 2-Propyl-6-heptenoic acid

HRID 325814Notes

Reaction equation

HRID 325814 reaction equation
[CH2:1]([CH:4]([CH2:9][CH2:10][CH2:11][CH:12]=[CH2:13])[C:5]([O:7]C)=[O:6])[CH2:2][CH3:3].[OH-].[Na+].O>C(O)C>[CH2:1]([CH:4]([CH2:9][CH2:10][CH2:11][CH:12]=[CH2:13])[C:5]([OH:7])=[O:6])[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 20462871Methyl 2-propyl-6-heptenoate

Product 1

HCID 204628752-Propyl-6-heptenoic acidYield 75.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of methyl 2-propyl-6-heptenoate (1.8 g), sodium hydroxide (0.65 g), water (2 ml) and ethanol (100 ml) was heated under reflux for 2 hours. The solvent was removed under reduced pressure and the resulting residue was shaken with water and hexane. The aqueous layer was acidified with concentrated hydrochloric acid and extracted with ethyl acetate. The organic layer was dried and concentrated to give oil of 2-propyl-6-heptenoic acid (1.25 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. customThe solvent was removed under reduced pressure
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a2d9b0c1f6984e6f81515ebe112d4275
Source dataset
uspto-grants-1984_04
Patent number
US04443365

Reaction notes

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