Hydrochloric Acid → HCID 21781768, compound

HRID 1402827Notes

Reaction equation

HRID 1402827 reaction equation
[OH-].[Na+].Cl.[S:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[CH:9]([CH2:14][C:15]([OH:17])=[O:16])[CH2:10][C:11]([OH:13])=O>C(Cl)(=O)C>[S:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[CH:9]1[CH2:10][C:11](=[O:13])[O:17][C:15](=[O:16])[CH2:14]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21770061HCID 21770061, compound

Product 1

HCID 21781768HCID 21781768, compound

Reagents, catalysts & solvents 1

HCID 6367Acetyl chlorideSolvent

Procedure

To a solution of commercial 2-thiophen-carboxaldehyde (22.4 g) and ethyl acetoacetate (50.5 ml) in ethanol (40 ml) piperidine (4 ml) was added with stirring at rt. The solution was kept at rt for 3 d to form a precipitate. After cooling in the refrigerator the yellow solid was crushed, collected by suction filtration, and washed with ethanol. Drying in vacuo affords 31 g of a faint yellowish solid (the bis-adduct of acetoacetate to the aldehyde). The powdered solid was added in portions to 40% NaOH (500 g) with stirring. The resulting orange coloured slurry was stirred at reflux for 2 h. After cooling in an ice bath the mixture was acidified by portionwise addition of conc. HCl (440 ml) to give a colourless precipitate. The solid was collected by suction filtration and washed with water. After drying in vacuo 3-(2-thienyl)glutaric acid (9.7 g) was obtained. The suspension of finely divided 3-(2-thienyl)glutaric acid in acetyl chloride (17 ml) was heated to reflux with stirring for 1 h. After cooling to rt precipitation of the product is induced by addition of petrol ether (100 ml). The precipitate is isolated by suction filtration, washed with petrol ether, and dried in vacuo to give 3-(2-thienyl)glutaric anhydride (8.2 g) as colourless crystals.

Workup

  1. stirringThe resulting orange coloured 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-thienyl)glutaric acid (9.7 g)
  8. customwas obtained
  9. temperaturewas heated
  10. temperatureto reflux
  11. stirringwith stirring for 1 h
  12. customprecipitation of the product
  13. additionis induced by addition of petrol ether (100 ml)
  14. customThe precipitate is isolated by suction filtration
  15. washwashed with petrol ether
  16. customdried in vacuo

Sources & evidence

ORD record
ord-3146dbd740454c12b2401f627bd3b995
Source dataset
uspto-grants-2014_12
Patent number
US08912186B2

Reaction notes

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