p-Toluenesulfonic acid → Ethyl 5-nitro-2-furoate

HRID 850968Notes

Reaction equation

HRID 850968 reaction equation
[N+:1]([C:4]1[O:8][C:7]([C:9]([OH:11])=[O:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:12]1(C)C=CC(S(O)(=O)=O)=C[CH:13]=1>C(O)C>[N+:1]([C:4]1[O:8][C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 125775-Nitro-2-Furoic Acid

Product 1

HCID 70341Ethyl 5-nitro-2-furoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 39 g. of 5-nitro-2-furancarboxylic acid in 200 ml. of ethanol is added 2 ml. of p-toluenesulfonic acid. The reaction is heated for 48 hours. The reaction mixture is evaporated and methylene chloride is added to the residue. The solution is extracted with 10% sodium bicarbonate and dried over anhydrous sodium sulfate. The solution is concentrated and then filtered through Magnesol. The product is obtained by recrystallization from methylene chloride and hexane.

Workup

  1. temperatureThe reaction is heated for 48 hours
  2. customThe reaction mixture is evaporated
  3. additionmethylene chloride is added to the residue
  4. extractionThe solution is extracted with 10% sodium bicarbonate
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe solution is concentrated
  7. filtrationfiltered through Magnesol
  8. customThe product is obtained by recrystallization from methylene chloride and hexane

Sources & evidence

ORD record
ord-bb6b90736a6742b2b24c32418227d738
Source dataset
uspto-grants-1983_05
Patent number
US04382143

Reaction notes

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