Hydrochloric Acid → Furaneol

HRID 1449126Notes

Reaction equation

HRID 1449126 reaction equation
[C:1]([C:6]1(C)[C:10](=[O:11])[C:9]([OH:12])=[C:8]([CH3:13])[O:7]1)(OCC)=O.[OH-].[Na+].Cl>O>[OH:11][C:10]1[C:9](=[O:12])[CH:8]([CH3:13])[O:7][C:6]=1[CH3:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 203499522-Carbethoxy-2,5-dimethyl-3-oxo-4-hydroxy-2H-furan

Product 1

HCID 19309FuraneolYield 71.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

A solution of 9 g of 2-carbethoxy-2,5-dimethyl-3-oxo-4-hydroxy-2H-furan and 5.4 g of sodium hydroxide in 50 ml of water is kept at room temperature under nitrogen for 20 hours. The reaction mixture is acidified with hydrochloric acid, then stirred at 30° C. for an hour and continuously extracted for 6 hours with ether. The ether extract is dried and the solvent is removed under vacuum, the residue is dissolved in a mixture of 5 ml of dry ether and 5 ml of dry pentane. The solution is cooled to -10° C. and filtered. The solid product is dried, yielding 4.1 g (70%) of 4-hydroxy-2,5-dimethyl-3-oxo-2H-furan. The isolated product is identical (NMR and IR) with a sample of 4-hydroxy-2,5-dimethyl-3-oxo-2H-furan prepared from rhamnose (loc cit). M.p. 82°-84° C.

Workup

  1. extractioncontinuously extracted for 6 hours with ether
  2. extractionThe ether extract
  3. customis dried
  4. customthe solvent is removed under vacuum
  5. dissolutionthe residue is dissolved in a mixture of 5 ml of dry ether and 5 ml of dry pentane
  6. temperatureThe solution is cooled to -10° C.
  7. filtrationfiltered
  8. customThe solid product is dried

Sources & evidence

ORD record
ord-0fdfcb3e36d9455ebc6d22d99979ff12
Source dataset
uspto-grants-1980_02
Patent number
US04189439

Reaction notes

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