Hydrochloric Acid → HCID 10198445, compound

HRID 542632Notes

Reaction equation

HRID 542632 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 aluminium 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 layer 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-f11fc336213b43eb9cddb993fd3ab206
Source dataset
uspto-grants-1987_04
Patent number
US04658055

Reaction notes

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