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

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

Reactant 6

HCID 313Hydrochloric Acid

HCID 768Hydrogen Cyanide

HCID 7860Glyoxal

HCID 9032Potassium Cyanide

HCID 10340Sodium Carbonate

HCID 120975-Methylfurfural

Product 1

HCID 1558752-Furanacetic acid, 5-methyl-

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.