Sulfuric Acid → 3-(4-Chlorophenyl)-2,5-furandione

HRID 1355336Notes

Reaction equation

HRID 1355336 reaction equation
S(=O)(=O)(O)[OH:2].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:18]#N)=[CH:14][C:15]([O-:17])=[O:16])=[CH:9][CH:8]=1.[K+]>C(O)=O>[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:18](=[O:2])[O:16][C:15](=[O:17])[CH:14]=2)=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 69861887HCID 69861887, compound

Product 1

HCID 5859973-(4-Chlorophenyl)-2,5-furandione

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
50 °C

Procedure

With stirring, 80 ml of concentrated sulfuric acid were added dropwise to 138 g (0.57 mol) potassium 3-(4-chlorophenyl)-3-cyanoacrylate in 1.2 l of 88% strength formic acid. During the addition, the temperature increased to 50° C. The mixture was refluxed for 3 h and, after cooling, put into 10 l of ice-water and then stirred for 1 h, and the product was filtered off, washed with water and dried under reduced pressure. Yield: 86.0 g of m.p. 144-145° C.

Workup

  1. additionDuring the addition
  2. temperatureThe mixture was refluxed for 3 h
  3. temperatureafter cooling
  4. stirringstirred for 1 h
  5. filtrationthe product was filtered off
  6. washwashed with water
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-105cf9d98cf64dc2b15039a5b806cae9
Source dataset
uspto-grants-2003_07
Patent number
US06586369B1

Reaction notes

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