Hydrochloric Acid → Furaneol

HRID 36059

Reaction equation

HRID 36059 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[O:8][C:7]([C:9](OC)=O)=[C:6]([OH:13])[C:5]=1[OH:14].CC1OC(C(OCC)=O)=C(O)C=1O.S(OC)(OC)(=O)=O.Cl>O>[CH3:3][CH:4]1[C:5](=[O:14])[C:6]([OH:13])=[C:7]([CH3:9])[O:8]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 54688627Methyl 5-methyl-3,4-dihydroxy-2-furoateHCID 54719681Ethyl 5-methyl-3,4-dihydroxy-2-furoate

Product 1

HCID 19309FuraneolYield 76.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 32 g of sodium hydroxide and 33 g of a mixture containing 37.1% of methyl 5-methyl-3,4-dihydroxy-2-furoate and 52.1% of ethyl 5-methyl-3,4-dihydroxy-2-furoate in 320 ml of water was allowed to stand at room temperature for 20 hours. To the resulting mixture is added at 0° C. in one hour 25.2 g of dimethyl sulphate followed by an additional stirring period of three hours at 0° C. The pH of the solution was adjusted to 6.5 by the addition of concentrated hydrochloric acid solution. Extraction with methyl t-butyl ether yielded 18.1 g of 2,5-dimethyl-4-hydroxy-3[2H] furanone of 88.8% purity (molar yield 76.6%).

Workup

  1. extractionExtraction with methyl t-butyl ether

Sources & evidence

ORD record
ord-e60933f0dafd4979a04714237e90ef77
Source dataset
uspto-grants-1995_05
Patent number
US05412121

Linked notes

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