Hydrochloric Acid → 4-Ethylhexa-2,4-dienoic acid

HRID 1656802Notes

Reaction equation

HRID 1656802 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+].Cl>CO.O>[CH2:11](/[C:3](=[CH:1]\[CH3:2])/[CH:4]=[CH:5]/[C:6]([OH:8])=[O:7])[CH3:12]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10899087ethyl (E,E)-4-ethyl-2,4-hexadienoate

Product 1

HCID 109425234-Ethylhexa-2,4-dienoic acidYield 97.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 20.0 kg (119 mol) of ethyl (E,E)-4-ethyl-2,4-hexadienoate in 15 l of methanol is added a solution of 6.0 kg (150 mol) of sodium hydroxide in 60 l of water. The mixture is heated at 50°-55° C. for 1 hour and then cooled to 20°~25° C., poured into a 8%-hydrochloric acid solution at same temperature. The precipitate formed is collected by filtration, washed with 200 l of water and dried in vacuo overnight to give 16.2 kg of (E,E)-4-ethyl-2,4-hexadienoic acid (Yield 97.4%).

Workup

  1. temperatureThe mixture is heated at 50°-55° C. for 1 hour
  2. temperaturecooled to 20°~25° C.
  3. customThe precipitate formed
  4. filtrationis collected by filtration
  5. washwashed with 200 l of water
  6. customdried in vacuo overnight

Sources & evidence

ORD record
ord-6868e27a1a3f4d1a8d7fadedfb4d0fbc
Source dataset
uspto-grants-1993_10
Patent number
US05254733

Reaction notes

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