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

HRID 1057298Notes

Reaction equation

HRID 1057298 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.[Al+3].[Cl-].[Cl-].[Cl-].[S:12]1[CH:16]=[CH:15][CH:14]=[CH:13]1.Cl>[N+](C1C=CC=CC=1)([O-])=O>[S:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:1](=[O:7])[CH2:2][CH2:3][C:4]([OH:6])=[O:5]

Participants

6

Reactant 4

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

Product 1

HCID 783853-(2-Thenoyl)propionic acidYield 55%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent3×

Procedure

3.57 g (0.036 mol) of succinic anhydride, 10.46 g (0.036 mol) of AlCl3 and 35 ml of nitrobenzene are placed in a three-necked flask under nitrogen atmosphere, equipped with a magnetic stirrer and cooled on an ice bath. 2.85 ml (0.036 mol) of thiophene dissolved in 17 ml of nitrobenzene is then added a drop at a time. The yellow medium turns a uniform brown during addition. Stirring is maintained for 5 h at room temperature. The medium cooled on the ice bath is hydrolysed with 25 ml of HCl 36% diluted in 20 ml of ice water. The nitrobenzene is carried over with the steam and the residue that remains is absorbed in a solution of Na2CO3. Repeating steam distillation removes the volatile products and the remaining solvent. The aqueous phase is acidified then extracted with ether which is dried over MgSO4 and concentrated. The acid is obtained in the form of 3.6 g of bright pale-yellow flakes after recrystallization in water. Yield=55%.

Workup

  1. customequipped with a magnetic stirrer
  2. temperaturecooled on an ice bath
  3. additionis then added a drop at a time
  4. additionbrown during addition
  5. customthe residue that remains is absorbed in a solution of Na2CO3
  6. distillationRepeating steam distillation
  7. customremoves the volatile products
  8. extractionThe aqueous phase is acidified then extracted with ether which
  9. dry with materialis dried over MgSO4
  10. concentrationconcentrated
  11. customThe acid is obtained in the form of 3.6 g of bright pale-yellow flakes
  12. customafter recrystallization in water

Sources & evidence

ORD record
ord-e14b3ba051e442db9d718720bfe742cb
Source dataset
uspto-grants-2003_02
Patent number
US06514967B1

Reaction notes

Loading…