1,2-Dichloroethane → HCID 53913724, compound

HRID 1706045Notes

Reaction equation

HRID 1706045 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C@@H:5]12[C:14](=[O:15])[O:13][C:11](=[O:12])[C@H:6]1[CH2:7][CH2:8][CH2:9][CH2:10]2.Cl[CH2:17][CH2:18]Cl>>[O:12]=[C:11]([C@@H:6]1[CH2:7][CH2:8][CH2:9][CH2:10][C@H:5]1[C:14]([OH:13])=[O:15])[CH:17]=[CH2:18]

Participants

4

Reactant 3

HCID 111,2-DichloroethaneHCID 6451240Aluminum(III) ChlorideHCID 12261141(-)-trans-1,2-Cyclohexanedicarboxylic Anhydride

Product 1

HCID 53913724HCID 53913724, compound

Procedure

A mixture of aluminum chloride (66.7 g., 0.5 mole), trans-1,2-cyclohexanedicarboxylic anhydride (38.5 g., 0.25 mole) 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 mixture is poured into 900 ml. of 5% hydrochloric 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 material from the original organic layer and taken to dryness. The residue is heated with 300 ml. of 10% potassium carbonate on a steam bath for fifteen minutes. After cooling, the mixture is extracted three times with ether. The aqueous layer is acidified and the product trans-2-[1-oxo-2-propenyl]cyclohexanecarboxylic acid (31.6 g.) is extracted into ether, dried and concentrated in vacuo. The crude crystalline trans-2-(1-oxo-2-propenyl)cyclohexanecarboxylic acid is recrystallized from ether-hexane, m.p. 101°-102°.

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 mixture 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. temperatureThe residue is heated with 300 ml
  9. waitof 10% potassium carbonate on a steam bath for fifteen minutes
  10. temperatureAfter cooling
  11. extractionthe mixture is extracted three times with ether
  12. extractionthe product trans-2-[1-oxo-2-propenyl]cyclohexanecarboxylic acid (31.6 g.) is extracted into ether
  13. customdried
  14. concentrationconcentrated in vacuo
  15. customThe crude crystalline trans-2-(1-oxo-2-propenyl)cyclohexanecarboxylic acid is recrystallized from ether-hexane, m.p. 101°-102°

Sources & evidence

ORD record
ord-57997cf374414bf7af05c6eabdac86b8
Source dataset
uspto-grants-1980_06
Patent number
US04206137

Reaction notes

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