Sulfuric Acid → 2-(Furan-2-yl)-3-methylbutanoic acid

HRID 1655760Notes

Reaction equation

HRID 1655760 reaction equation
C([O:3][C:4](=[O:19])[C:5]([C:14]1[O:15][CH:16]=[CH:17][CH:18]=1)([CH:11]([CH3:13])[CH3:12])C(OCC)=O)C.[OH-].[Na+].S(=O)(=O)(O)O>CS(C)=O>[O:15]1[CH:16]=[CH:17][CH:18]=[C:14]1[CH:5]([CH:11]([CH3:13])[CH3:12])[C:4]([OH:19])=[O:3]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 536718092-Furyl-2-isopropylmalonic acid diethyl ester

Product 1

HCID 197908462-(Furan-2-yl)-3-methylbutanoic acidYield 98.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

240.6 g (0.9 mol) of 2-furyl-2-isopropylmalonic acid diethyl ester were dissolved in 500 ml of dimethyl sulfoxide, treated with 2000 ml of 2N sodium hydroxide solution and heated to reflux for 2 hours. After cooling, o the reaction mixture was poured into dilute sulfuric acid and extracted exhaustively with ether. The organic extracts were thereafter dried and the solvent was evaporated under reduced pressure, to obtain 148.7 g (98%) of (±) 2-(2-furyl)-3-methyl- butyric acid in the form of a thick yellowish oil.

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. temperatureAfter cooling, o the reaction mixture
  4. extractionextracted exhaustively with ether
  5. customThe organic extracts were thereafter dried
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b414730056a548e08079aab95ebcceec
Source dataset
uspto-grants-1993_10
Patent number
US05250517

Reaction notes

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