Hydrochloric Acid → 2-Furanacetic acid, 5-methyl-

HRID 1421867Notes

Reaction equation

HRID 1421867 reaction equation
[C-]#N.[K+].[C:4](=[O:7])([O-])[O-:5].[Na+].[Na+].[CH3:10][C:11]1[O:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1.C(C=O)=O.Cl.C#N>O.O1CCOCC1>[CH3:15][C:14]1[O:17][C:11]([CH2:10][C:4]([OH:5])=[O:7])=[CH:12][CH:13]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 768Hydrogen CyanideHCID 7860GlyoxalHCID 9032Potassium CyanideHCID 10340Sodium CarbonateHCID 120975-Methylfurfural

Product 1

HCID 1558752-Furanacetic acid, 5-methyl-

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a solution of potassium cyanide (12.2 g, 0.187 mol) and sodium carbonate (36 g, 0.338 mol) in water (250 ml) was added 5-methyl furfural (7.5 ml, 75 mmol) in 1,4-dioxane (12 ml) followed by glyoxal busulphite (3.0 g, 0.289 mol) and water (240 ml). After stirring for 21/2 hr at room temperature, the reaction was worked up by adding 5N HCl(aq) to the reaction mixture carefully (HCN↑) until the pH fell to ≈1-2. Stirring was continued for 1 hr after which time, no more gas was evolved.

Workup

  1. stirringStirring
  2. waitwas continued for 1 hr

Sources & evidence

ORD record
ord-3b0e60a9e0974822aa38a279c7d73414
Source dataset
uspto-grants-2000_06
Patent number
US06080745

Reaction notes

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