Acetaldehyde → 1,4-Anhydro-6-deoxy-1,4-dimethylhex-1-en-3-ulose

HRID 1605745Notes

Reaction equation

HRID 1605745 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:12])[CH3:11].C(O)(=O)C(O)=O>O>[OH:12][CH:10]([C:4]1([CH3:9])[C:5](=[O:8])[C:6]([OH:7])=[C:2]([CH3:1])[O:3]1)[CH3:11]

Participants

5

Reactant 3

HCID 177AcetaldehydeHCID 971Oxalic AcidHCID 19309Furaneol

Product 1

HCID 1035781,4-Anhydro-6-deoxy-1,4-dimethylhex-1-en-3-uloseYield 54.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a round-bottomed flask equipped with a stirrer and a condensor, 12.8 g (0.1 mole) of 2,5-dimethyl-4-hydroxy-3-(2H)-furanone and 44 g (1.0 mole) of acetaldehyde were introduced into a solution of 3.0 g of oxalic acid in 100 ml of water. The mixture was stirred and refluxed for 1 hour. After cooling, the mixture was extracted 5 times with 25 ml portions of chloroform and the organic solvent was evaporated off. The residue was purified by chromatography on 50 g of polyamide. After elution by means of a 50/50 mixture of ether and petroleum ether, 9.4 g of the title compound was obtained (which corresponds to a yield of 54%). Recrystallization from ether gave the pure product with m.p. 112-114°C).

Workup

  1. customIn a round-bottomed flask equipped with a stirrer
  2. temperaturerefluxed for 1 hour
  3. temperatureAfter cooling
  4. extractionthe mixture was extracted 5 times with 25 ml portions of chloroform
  5. customthe organic solvent was evaporated off
  6. customThe residue was purified by chromatography on 50 g of polyamide
  7. washAfter elution
  8. additionby means of a 50/50 mixture of ether and petroleum ether

Sources & evidence

ORD record
ord-6a30978656994071917bb354d6708c8c
Source dataset
uspto-grants-1976_04
Patent number
US03950565

Reaction notes

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