tags
glyoxylatehydroxymandelichydrochloricdehydrated aciddiethylpotassiummandelicphenethylamineoxalic acidglyoxylicphenolaldehydeoxalic acid dihydrateoxalicpotassium phenylatemagnesium

video tutorial Glyoxylic acid and experimental prep of hydroxymandelic acid

  • Goal: evaluate a reaction between glyoxylate (made from oxalic acid and magnesium) and phenol under basic conditions to form a substituted mandelic/hydroxymandelic acid derivative.
  • Procedure highlights: dissolve oxalic acid dihydrate in water, add magnesium metal to generate glyoxylate; use potassium hydroxide to precipitate magnesium as Mg(OH)2 and generate potassium glyoxylate; prepare potassium phenolate from phenol using KOH; combine glyoxylate filtrate with phenolate solution; monitor the mixture; acidify with HCl to pH ~3; separate and chill to crystallize; filter and dry.
  • Result: 3.2 g of a crystalline white solid isolated; solid tested acidic to indicator paper.
  • Characterization: solubility tests suggest the product is not simply oxalic acid (low water solubility, insoluble in ether and dichloromethane, some solubility in sodium hydroxide); hydroxymandelic acid is reported to be white or red depending on source; yield potentially 6.5% relative to starting phenol if the product matches literature, but this is uncertain and no reliable yield is obtained.
  • Conclusion: identity of the product remains uncertain; if the reaction can be made reliable, it could be a useful route to phenethylamine-type compounds; additional information or conditions are needed to confirm identity and improve yield.

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