Sodium Dithionite → 2,2'-Bithiophene-5-carboxylic acid

HRID 1450613Notes

Reaction equation

HRID 1450613 reaction equation
[O-]Cl.[Na+].[C:4]([C:7]1[S:11][C:10]([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)=[CH:9][CH:8]=1)(=[O:6])C.[O-:17]S(S([O-])=O)=O.[Na+].[Na+]>>[C:4]([C:7]1[S:11][C:10]([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)=[CH:9][CH:8]=1)([OH:6])=[O:17]

Participants

4

Reactant 3

HCID 24489Sodium DithioniteHCID 6064225-Acetyl-2,2'-bithienylHCID 23665760Sodium Hypochlorite

Product 1

HCID 1509652,2'-Bithiophene-5-carboxylic acid

Procedure

35 ml of NaOCl solution was heated to 55° C. and 5-acetyl-2,2'-bithiophene was then added and stirred at 60°-70° C. for 2 hours. Then the reaction solution was cooled by ice bath and aqueous Na2S2O4 solution was added for removing the residual NaOCl. The reaction mixture was acidified by HCl(aq) and filtered to obtain golden product. The product was further recrystallized with 95% ethanol. The melting point of the product was 183-184%.

Workup

  1. temperatureThen the reaction solution was cooled by ice bath
  2. customfor removing the residual NaOCl
  3. filtrationfiltered
  4. customto obtain golden product
  5. customThe product was further recrystallized with 95% ethanol

Sources & evidence

ORD record
ord-560a5760db2f4c50a9267b1500ae651c
Source dataset
uspto-grants-1997_02
Patent number
US05602170

Reaction notes

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