Formaldehyde → HCID 20373310, compound

HRID 1605748Notes

Reaction equation

HRID 1605748 reaction equation
[CH3:1][CH:2]1[C:6](=[O:7])[C:5]([OH:8])=[C:4]([CH3:9])[O:3]1.[CH2:10]=[O:11].C(O)(=O)C(O)=O>O>[OH:11][CH2:10][C:4]1([CH3:9])[C:5](=[O:8])[C:6]([OH:7])=[C:2]([CH3:1])[O:3]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 971Oxalic AcidHCID 19309Furaneol

Product 1

HCID 20373310HCID 20373310, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 10 g of 2,5-dimethyl-4-hydroxy-3-(2H)-furanone, 20 ml of a 37% formaldehyde aqueous solution, 50 ml of water and 0.7 g of oxalic acid was stirred for 18 hours at room temperature. After working up the reaction mixture, the crude reaction product was purified by column chromatography over polyamide. Elution with pentane-dichloromethane 80/20 yielded the pure 2-hydroxymethyl-2,5-dimethyl-4-hydroxy-3-(2H)-furanone, which was recrystallized from ethyllactate; m.p. 124°-125°C.

Workup

  1. customthe crude reaction product
  2. customwas purified by column chromatography over polyamide
  3. washElution with pentane-dichloromethane 80/20

Sources & evidence

ORD record
ord-71299bcc1865475b9bc0315828726052
Source dataset
uspto-grants-1976_04
Patent number
US03950565

Reaction notes

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