Hydrochloric Acid → Ethyl hepta-2,4-dienoate

HRID 1284167Notes

Reaction equation

HRID 1284167 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][CH:3]=[C:4]=[CH:5][CH2:6][CH3:7].Cl>C(O)CC.[OH-].[K+]>[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH2:6][CH3:7]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 21515746HCID 21515746, compound

Product 1

HCID 54483010Ethyl hepta-2,4-dienoateYield 92%

Reagents, catalysts & solvents 2

HCID 14797Potassium HydroxideCatalystHCID 10311-PropanolSolvent

Procedure

20 g of the ethyl 3,4-heptadienoate obtained in Example 1 was agitated at 40°C. for 2 hours in 80 ml of propanol in the presence of 3 ml of 4N KOH as a catalyst. The resulting reaction mixture was neutralized with 4N HCl, dried and distilled. Ethyl 2,4-heptadienoate was obtained in a yield of 92% from a fraction boiling at 64.5°C. under 2.5 mm Hg. The double bond at the 2-position was of the trans-form and the double bond at the 4-position was composed of 55% of the cis-form and 45% of the trans-form.

Workup

  1. customThe resulting reaction mixture
  2. customdried
  3. distillationdistilled

Sources & evidence

ORD record
ord-675605aa90d3418198a6c98e09e318ff
Source dataset
uspto-grants-1976_08
Patent number
US03978100

Reaction notes

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