Hydrochloric Acid → HCID 54758303, compound

HRID 1402817Notes

Reaction equation

HRID 1402817 reaction equation
C(C1C=CC(C=O)=CC=1)CC.C(OCC)(=O)CC(C)=O.[OH-].[Na+].Cl.[CH2:24]([C:27]1[CH:32]=[CH:31][C:30]([CH:33]([CH2:38][C:39]([OH:41])=[O:40])[CH2:34][C:35]([OH:37])=O)=[CH:29][CH:28]=1)[CH2:25][CH3:26]>C(O)C.C(Cl)(=O)C>[CH2:24]([C:27]1[CH:28]=[CH:29][C:30]([CH:33]2[CH2:34][C:35](=[O:37])[O:41][C:39](=[O:40])[CH2:38]2)=[CH:31][CH:32]=1)[CH2:25][CH3:26]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8868Ethyl AcetoacetateHCID 14798Sodium HydroxideHCID 1200474-PropylbenzaldehydeHCID 66759382HCID 66759382, compound

Product 1

HCID 54758303HCID 54758303, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6367Acetyl chlorideSolvent

Procedure

To a solution of commercial 4-propyl-benzaldehyde (5 g) and ethyl acetoacetate (8.77 g) in ethanol (10 ml) piperidine (1 ml) was added with stirring at rt. The yellow solution was kept at rt overnight. The precipitate was collected by suction filtration and washed with ethanol. After drying in vacuo 8.75 g of a faint yellowish solid (the bis-adduct of acetoacetate to the benzaldehyde) was isolated. The finely divided solid was added in portions to 40% NaOH (120 g) with stirring. The resulting yellow slurry was stirred at reflux for 2 h. After cooling in an ice bath the mixture was acidified by portionwise addition of conc. HCl (110 ml) to give a precipitate. The solid was collected by suction filtration and washed with water. After drying in vacuo 3-(4-propylphenyl)glutaric acid (4.89 g) was obtained. The suspension of finely divided 3-(4-propylphenyl)glutaric acid in acetyl chloride (7 ml) was heated to reflux with stirring for 1 h. After cooling to rt precipitation of the product is completed by addition of petrol ether (50 ml). The precipitate is isolated by suction filtration, washed with petrol ether, and recrystallised to give 3-(4-propylphenyl)glutaric anhydride (2.5 g) as colourless crystals.

Workup

  1. filtrationThe precipitate was collected by suction filtration
  2. washwashed with ethanol
  3. dry with materialAfter drying in vacuo 8.75 g of a faint yellowish solid (the bis-adduct of acetoacetate to the benzaldehyde)
  4. customwas isolated
  5. stirringwith stirring
  6. stirringThe resulting yellow slurry was stirred
  7. temperatureat reflux for 2 h
  8. temperatureAfter cooling in an ice bath the mixture
  9. customto give a precipitate
  10. filtrationThe solid was collected by suction filtration
  11. washwashed with water
  12. dry with materialAfter drying in vacuo 3-(4-propylphenyl)glutaric acid (4.89 g)
  13. customwas obtained
  14. temperaturewas heated
  15. temperatureto reflux
  16. stirringwith stirring for 1 h
  17. temperatureAfter cooling to rt
  18. customprecipitation of the product
  19. additionis completed by addition of petrol ether (50 ml)
  20. customThe precipitate is isolated by suction filtration
  21. washwashed with petrol ether
  22. customrecrystallised

Sources & evidence

ORD record
ord-f67d850bb3fc46278d68d30e1b70c0c0
Source dataset
uspto-grants-2014_12
Patent number
US08912186B2

Reaction notes

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