2-Thiophenecarboxaldehyde → HCID 86756151, compound

HRID 1276546Notes

Reaction equation

HRID 1276546 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[O:7].[C:8]([O:11]C(=O)C)(=[O:10])[CH3:9]>S(=O)(=O)(O)O.C(Cl)(Cl)Cl>[C:8]([OH:11])(=[O:10])[CH3:9].[C:8]([OH:11])(=[O:10])[CH3:9].[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[O:7]

Participants

5

Reactant 2

HCID 73642-ThiophenecarboxaldehydeHCID 7918Acetic Anhydride

Product 1

HCID 86756151HCID 86756151, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 6212ChloroformSolvent

Procedure

Thiophene-2-carboxaldehyde (5.66 g, 0.050 mol) was dissolved in an excess of acetic acid anhydride (10 ml) and 3 drops conc. sulfuric acid added under stirring. The resulting green mixture was allowed to react at room temperature for 2.5 hr. The reaction mixture was then diluted with CHCl3 (25 ml) before washing twice with 10% aqueous NaHCO3 (20 ml). The organic phase was dried (MgSO4) and evaporated. The crude product was dissolved in hexane, and insoluble impurities were removed. The hexane solution was then treated with activated charcoal, to give a colourless liquid. Evaporation of the solvent gave white or weakly pink crystals. The yield was 3.8 g, 35% of the theoretical. 1H- and 13C NMR (CDCl3), d (ppm) rel. to TMS: 7.93 (s, 1H, CH(OAc)2) 7.49, 7.27 and 7.02 (m, 3×1H, Ar-H) and 2.12 (s, 6H, CH3); 168.386, 137.867, 127.179,126.917 and 126.599 (Ar), 86.227 (CH(OAc)2) and 20.663 (CH3).

Workup

  1. additionadded
  2. customto react at room temperature for 2.5 hr
  3. washbefore washing twice with 10% aqueous NaHCO3 (20 ml)
  4. dry with materialThe organic phase was dried (MgSO4)
  5. customevaporated
  6. dissolutionThe crude product was dissolved in hexane
  7. custominsoluble impurities were removed
  8. additionThe hexane solution was then treated with activated charcoal
  9. customto give a colourless liquid
  10. customEvaporation of the solvent
  11. customgave white

Sources & evidence

ORD record
ord-b7605fa9e1cc49d38a9c0a5869bbd0f8
Source dataset
uspto-grants-2000_12
Patent number
US06166074

Reaction notes

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