Hydrochloric Acid → 3-(2-Thenoyl)propionic acid

HRID 66499Notes

Reaction equation

HRID 66499 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[N+](C1C=CC=CC=1)([O-])=O.[C:15]1(=[O:21])[O:20][C:18](=[O:19])[CH2:17][CH2:16]1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>>[O:21]=[C:15]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)[CH2:16][CH2:17][C:18]([OH:20])=[O:19]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 7416Nitrobenzene2×HCID 7922Succinic anhydrideHCID 8030ThiopheneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 783853-(2-Thenoyl)propionic acidYield 53%

Procedure

A solution of 0.3 mole of thiophene in 100 ml. of nitrobenzene is added dropwise with stirring to a cooled mixture of 30 g. (0.3 mole) of succinic anhydride, 87.8 g. (0.66 mole) of aluminum chloride and 300 ml. of nitrobenzene. The mixture is cooled and stirred for 30 minutes and then allowed to stand at room temperature overnight. The mixture is poured onto ice and 50 ml. of concentrated hydrochloric acid. The nitrobenzene is removed by steam distillation. The aqueous layer is decanted and the residue is mixed with 650 ml. of water and 20 g. of sodium carbonate. The mixture is heated, mixed with diatomaceous earth and filtered. The filtrate is acidified with concentrated hydrochloric acid and the solid which separates is filtered and washed with water. Recrystallization from water gives 53% of 4-oxo-4-(2-thienyl)butyric acid, m.p. 121°-123° C.

Workup

  1. temperatureThe mixture is cooled
  2. stirringstirred for 30 minutes
  3. additionThe mixture is poured onto ice and 50 ml
  4. customThe nitrobenzene is removed by steam distillation
  5. customThe aqueous layer is decanted
  6. additionthe residue is mixed with 650 ml
  7. temperatureThe mixture is heated
  8. additionmixed with diatomaceous earth
  9. filtrationfiltered
  10. filtrationthe solid which separates is filtered
  11. washwashed with water
  12. customRecrystallization from water

Sources & evidence

ORD record
ord-1036f0ebc64e4301a2900110351aacae
Source dataset
uspto-grants-1982_08
Patent number
US04342690

Reaction notes

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