Propanal → HCID 20373309, compound

HRID 1605749Notes

Reaction equation

HRID 1605749 reaction equation
[CH3:1][CH:2]1[C:6](=[O:7])[C:5]([OH:8])=[C:4]([CH3:9])[O:3]1.[CH:10](=[O:13])[CH2:11][CH3:12].C(O)(=O)C(O)=O>O>[OH:13][CH:10]([C:4]1([CH3:9])[C:5](=[O:8])[C:6]([OH:7])=[C:2]([CH3:1])[O:3]1)[CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 527PropanalHCID 971Oxalic AcidHCID 19309Furaneol

Product 1

HCID 20373309HCID 20373309, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 1.0 g of 2,5-dimethyl-4-hydroxy-3-(2H)-furanone, 5 g of propanal and 20 ml of water were added 0.2 g of oxalic acid and the mixture was stirred at room temperature for 25 hours and then extracted three times with chloroform. The chloroform extract was evaporated and the residue purified by column chromatography on polyamide using ether-pentane 10/90 as the eluent. Pure 2-(1-hydroxypropyl)-2,5-dimethyl-4-hydroxy-3-(2H)-furanone was obtained, which was recrystallized from ether-pentane 50/50; solid mass at room temperature.

Workup

  1. extractionextracted three times with chloroform
  2. extractionThe chloroform extract
  3. customwas evaporated
  4. customthe residue purified by column chromatography on polyamide

Sources & evidence

ORD record
ord-23fd828a407645b78598cf8178b6d9da
Source dataset
uspto-grants-1976_04
Patent number
US03950565

Reaction notes

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