Benzaldehyde → HCID 70622225, compound

HRID 1605746Notes

Reaction equation

HRID 1605746 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)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O.C(O)(=O)C(O)=[O:21]>O1CCOCC1>[OH:21][C:11]1([CH:12]=[CH:13][CH:14]=[CH:15][CH2:16]1)[CH2:10][C:4]1([CH3:9])[C:5](=[O:8])[C:6]([OH:7])=[C:2]([CH3:1])[O:3]1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 962WaterHCID 971Oxalic AcidHCID 19309Furaneol

Product 1

HCID 70622225HCID 70622225, compoundYield 205.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5 g of 2,5-dimethyl-4-hydroxy-3-(2H)-furanone and 10.6 g of benzaldehyde was added to a mixture of 20 ml of water, 20 ml of dioxan and 0.5 g of oxalic acid. The mixture was then refluxed for 4 hours, cooled and extracted with chloroform. The chloroform extract was evaporated and the residue purified by column chromatography over polyamide using ether - light petroleum 50/50 as the eluent; 2.7 g (30% yield) of the title compound was obtained which was recrystallized from chloroform, m.p. = 122°-124°C.

Workup

  1. temperatureThe mixture was then refluxed for 4 hours
  2. temperaturecooled
  3. extractionextracted with chloroform
  4. extractionThe chloroform extract
  5. customwas evaporated
  6. customthe residue purified by column chromatography over polyamide

Sources & evidence

ORD record
ord-b8c56ae1d9244cbd8c7c92879efc5901
Source dataset
uspto-grants-1976_04
Patent number
US03950565

Reaction notes

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