Oxalic Acid → Salicylaldehyde

HRID 2414466Notes

Reaction equation

HRID 2414466 reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][OH:4].C(O)(=O)C(O)=O.[C:12]1(C)[CH:17]=CC=[CH:14][CH:13]=1>>[CH:1](=[O:5])[C:2]1[C:3](=[CH:17][CH:12]=[CH:13][CH:14]=1)[OH:4]

Participants

4

Reactant 3

HCID 971Oxalic AcidHCID 1140TolueneHCID 104421,3-Propanediol

Product 1

HCID 6998Salicylaldehyde

Procedure

1,3-propanediol (228 g, 3.0 mol), and oxalic acid (4.5 g, 0.05 mol) were added to 400 mL toluene and heated to reflux for 8 hours in an apparatus equipped with a condenser and a Dean-Stark trap. After cooling, the solution was washed with NaHCO3 and distilled water, and the solution was dried over MgSO4. The product precipitated when the solvent was being evaporated. The solid was collected and dissolved in hot hexane. The solution was filtered through Celite® (a filter aid manufactured by Johns Manville Corp.), and the product was crystallized to give 108 g of an off-white solid.

Workup

  1. temperatureheated
  2. temperatureto reflux for 8 hours in an apparatus
  3. customequipped with a condenser
  4. temperatureAfter cooling
  5. washthe solution was washed with NaHCO3
  6. distillationdistilled water
  7. dry with materialthe solution was dried over MgSO4
  8. customThe product precipitated when the solvent
  9. customwas being evaporated
  10. customThe solid was collected
  11. dissolutiondissolved in hot hexane
  12. filtrationThe solution was filtered through Celite® (a filter aid
  13. custom), and the product was crystallized

Sources & evidence

ORD record
ord-e635972b403d4f2d8e3b33576d584204
Source dataset
uspto-grants-2004_11
Patent number
US06812352B2

Reaction notes

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