Hydrochloric Acid → HCID 10198445, compound

HRID 231921Notes

Reaction equation

HRID 231921 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]1(=[O:11])[O:10][C:8](=O)[CH2:7][CH2:6]1.C([O:15][C:16]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH:17]=1)(=O)C.Cl.[N+](C)([O-])=[O:26]>>[O:26]=[C:21]1[CH2:22][CH2:23][C:16](=[O:15])[CH:20]1[CH2:19][CH2:18][CH2:17][CH2:8][CH2:7][CH2:6][C:5]([OH:10])=[O:11]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 6375NitromethaneHCID 7922Succinic anhydrideHCID 3023180HCID 3023180, compoundHCID 6451240Aluminum(III) Chloride

Product 1

HCID 10198445HCID 10198445, compound

Procedure

To a solution of 2.7 g of aluminum chloride in 15 ml of nitromethane, 1.0 g of succinic anhydride was added, and then 1.7 g of 1-cyclooctenyl acetate was added dropwise under cooling. The resultant mixture was stirred at room temperature overnight and refluxed with stirring for four hours. The mixture was cooled, poured into 50 ml of 1N hydrochloric acid containing ice, and extracted four times with 30 ml of ethyl acetate. The organic layer was extracted twice with 30 ml of a saturated aqueous sodium bicarbonate solution. The aqueous layer was washed with ethyl acetate at pH 7. The aqueous was adjusted to pH 2 with 6N hydrochloric acid, and again extracted four times with 30 ml of ethyl acetate. The extract was dried and concentrated. The residue was washed with water to give 0.2 g of 7-(2,5-dioxocyclopentyl) heptanoic acid. This product had a melting point of 105° to 122° C.

Workup

  1. temperatureunder cooling
  2. temperaturerefluxed
  3. temperatureThe mixture was cooled
  4. additioncontaining ice
  5. extractionextracted four times with 30 ml of ethyl acetate
  6. extractionThe organic layer was extracted twice with 30 ml of a saturated aqueous sodium bicarbonate solution
  7. washThe aqueous layer was washed with ethyl acetate at pH 7
  8. extractionagain extracted four times with 30 ml of ethyl acetate
  9. customThe extract was dried
  10. concentrationconcentrated
  11. washThe residue was washed with water

Sources & evidence

ORD record
ord-bc84cc9f939f471da520bb265e00cb7e
Source dataset
uspto-grants-1989_07
Patent number
US04849535

Reaction notes

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