Propanal → HCID 20373309, compound

HRID 1834407Notes

Reaction equation

HRID 1834407 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-ef58dc44cec14a37a8fed6f95878f1d7
Source dataset
uspto-grants-1978_01
Patent number
US04070381

Reaction notes

Loading…