Hydrochloric Acid → HCID 82126207, compound

HRID 1402812Notes

Reaction equation

HRID 1402812 reaction equation
[OH-].[Na+].Cl.[CH3:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH:11]([CH2:16][C:17]([OH:19])=[O:18])[CH2:12][C:13]([OH:15])=O>C(Cl)(=O)C.ClCCl>[CH3:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH:11]1[CH2:12][C:13](=[O:15])[O:19][C:17](=[O:18])[CH2:16]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57747865HCID 57747865, compound

Product 1

HCID 82126207HCID 82126207, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6367Acetyl chlorideSolvent

Procedure

To a solution of commercial 2-methylbenzaldehyde (18 g) and ethyl acetoacetate (39 g) in ethanol (30 ml) piperidine (3 ml) was added with stirring at rt. The mixture was kept at rt for 2 d. The precipitate was collected by suction filtration, washed with ethanol, and dried in vacuo to give 25.66 g of a yellowish solid (the bis-adduct of acetoacetate to the benzaldehyde). The powdered solid was added in portions to 40% NaOH (300 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 (280 ml) to give a colourless precipitate. The solid was collected by suction filtration and washed with water. After drying in vacuo 3-(2-methylphenyl)glutaric acid (9.01 g) was obtained. The suspension of finely divided 3-(2-methylphenyl)glutaric acid in acetyl chloride (14.4 ml) was heated to reflux with stirring for 2 h. After cooling to rt petrol ether (50 ml) is added and the mixture is kept in the refrigerator for 12 h. The precipitate is isolated by suction filtration, washed with petrol ether, and dried in vacuo to give a crude which is dissolved in dichloromethane (400 ml). Insolubles are removed by filtration and the filtrate is concentrated in vacuo to provide 3-(2-methylphenyl)glutaric anhydride (6.79 g) as colourless solid.

Workup

  1. stirringThe resulting yellow slurry was stirred
  2. temperatureat reflux for 2 h
  3. temperatureAfter cooling in an ice bath the mixture
  4. customto give a colourless precipitate
  5. filtrationThe solid was collected by suction filtration
  6. washwashed with water
  7. dry with materialAfter drying in vacuo 3-(2-methylphenyl)glutaric acid (9.01 g)
  8. customwas obtained
  9. temperaturewas heated
  10. temperatureto reflux
  11. stirringwith stirring for 2 h
  12. additionis added
  13. customThe precipitate is isolated by suction filtration
  14. washwashed with petrol ether
  15. customdried in vacuo
  16. customto give a crude which
  17. customInsolubles are removed by filtration
  18. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-a777610e3e5247d1a908ec75c1380bed
Source dataset
uspto-grants-2014_12
Patent number
US08912186B2

Reaction notes

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