1,2-Dichloroethane → 4-Oxo-5-hexenoic Acid

HRID 1706049Notes

Reaction equation

HRID 1706049 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]1(=[O:11])[O:10][C:8](=[O:9])[CH2:7][CH2:6]1.Cl[CH2:13][CH2:14]Cl>>[O:11]=[C:5]([CH:13]=[CH2:14])[CH2:6][CH2:7][C:8]([OH:10])=[O:9]

Participants

4

Reactant 3

HCID 111,2-DichloroethaneHCID 7922Succinic anhydrideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 30286144-Oxo-5-hexenoic Acid

Procedure

[cf. J. Chem. Soc., 3922 (1958)]. A mixture of aluminum chloride (66.7 g., 0.5 M), succinic anhydride (25 g., 0.25 M) and 1,2-dichloroethane (1 liter) in a 2 liter 3 neck flask equipped with a gas inlet tube, a mechanical stirrer and a drying tube is stirred rapidly and ethylene is bubbled in for 4.5 hours. This is poured into 900 ml. 5% hydrochlorc acid and ice. The layers are separated and the organic layer is washed with water and taken to dryness in vacuo. The aqueous layer is extracted with ether (300 ml.). This extract is washed with water and combined with the material from the original organic layer. After removal of solvent, 150 ml. of 10% potassium carbonate solution is added and the mixture is heated on a steam cone for 15 minute. After cooling, the product 4-oxo-5-hexenoic acid is extracted into ether, dried and freed of solvent in vacuo leaving 10.9 g. (34%) of brownish liquid which solidifies on standing. This is distilled to give 7.1 g. (22%) of colorless liquid which solidifies on standing, b.p. ~120°-130°/0.5 mm.

Workup

  1. customequipped with a gas inlet tube, a mechanical stirrer and a drying tube
  2. customethylene is bubbled in for 4.5 hours
  3. additionThis is poured into 900 ml
  4. customThe layers are separated
  5. washthe organic layer is washed with water
  6. extractionThe aqueous layer is extracted with ether (300 ml.)
  7. washThis extract is washed with water
  8. customAfter removal of solvent, 150 ml
  9. additionof 10% potassium carbonate solution is added
  10. temperaturethe mixture is heated on a steam cone for 15 minute
  11. temperatureAfter cooling
  12. extractionthe product 4-oxo-5-hexenoic acid is extracted into ether
  13. customdried
  14. customleaving 10.9 g
  15. distillationThis is distilled
  16. customto give 7.1 g

Sources & evidence

ORD record
ord-9c9ae727da254acf9be7b3d34eddd1a4
Source dataset
uspto-grants-1980_06
Patent number
US04206137

Reaction notes

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