Sodium Hydroxide → 4-Ethylhexa-2,4-dienoic acid

HRID 868218Notes

Reaction equation

HRID 868218 reaction equation
[CH2:1](/[C:3](=[CH:11]\[CH3:12])/[CH:4]=[CH:5]/[C:6]([O:8]CC)=[O:7])[CH3:2].[OH-].[Na+]>CO>[CH2:11](/[C:3](=[CH:1]\[CH3:2])/[CH:4]=[CH:5]/[C:6]([OH:8])=[O:7])[CH3:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10899087ethyl (E,E)-4-ethyl-2,4-hexadienoate

Product 1

HCID 109425234-Ethylhexa-2,4-dienoic acidYield 96.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl (E,E)-4-ethyl-2,4-hexadienoate (134 g) was dissolved in methanol (200 ml) and 1N aqueous sodium hydroxide (880 ml) was added to the solution. The resulting mixture was stirred at room temperature for 20 hours under nitrogen atmosphere. After removal of methanol, the residual aqueous solution was washed with ether. The aqueous layer was acidified with conc. hydrochloric acid and then extracted with three portions of ethyl acetate (500 ml×3). The combined extracts were washed with brine, dried over magnesium sulfate and then evaporated to dryness to give a white powder which was crystallized from ether to give (E,E)-4-ethyl-2,4-hexadienoic acid (108 g).

Workup

  1. customAfter removal of methanol
  2. washthe residual aqueous solution was washed with ether
  3. extractionextracted with three portions of ethyl acetate (500 ml×3)
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to dryness
  7. customto give a white powder which
  8. customwas crystallized from ether

Sources & evidence

ORD record
ord-0f83c505a5f94b289846907a279f9dc4
Source dataset
uspto-grants-1988_10
Patent number
US04778804

Reaction notes

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