Hydrogen Peroxide → Glycolic Acid

Reaction equation

C(O)[C@H]1[O:7][C@H:6]([O:8][C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H:5]([OH:20])[C@@H:4]([OH:21])[C@@H:3]1[OH:22].O.[OH-].[Na+].OO>>[OH:21][C@H:4]([CH2:3][OH:22])[CH2:5][C:6]([OH:8])=[O:7].[C:6]([OH:8])(=[O:7])[CH2:5][OH:20]

Participants

Reactant 3

HCID 784Hydrogen Peroxide

HCID 14798Sodium Hydroxide

HCID 2723821(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(2R,3S,4R,5R,6R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxane-3,4,5-triol;hydrate

Product 2

HCID 757Glycolic Acid

HCID 10920498(S)-3,4-dihydroxybutyric acid

Conditions

Temperature: 70 °C

Procedure

Maltose monohydrate (0.10 g, 0.28 mmoles) was dissolved in 0.16M sodium hydroxide solution (5 ml, 0.8 mmoles) and 30% hydrogen peroxide (40 1, 0.37 mmoles) was added. The mixture was heated at 70° C. for 24 hours to produce (S)-3,4-dihydroxybutanoic acid and glycolic acid in the reaction mixture which can be separated by liquid chromatographic techniques if necessary or desired