Acetic Acid → 1,6-Dideoxyhexo-2,5-diulose

HRID 1092933Notes

Reaction equation

HRID 1092933 reaction equation
[CH3:1][C:2]([CH:4]=[O:5])=[O:3].O[CH2:7][C:8](=[O:10])[CH3:9].C(O)(=O)C.[OH2:15]>>[OH:15][CH:7]([CH:4]([OH:5])[C:2](=[O:3])[CH3:1])[C:8](=[O:10])[CH3:9]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 880MethylglyoxalHCID 962Water2×HCID 8299Hydroxyacetone

Product 1

HCID 780331,6-Dideoxyhexo-2,5-diuloseYield 56%

Procedure

A solution of methyl glyoxal 43% wt in water (2.00 g, 11.9 mmol), hydroxy-acetone (4.42 g, 59.7 mmol), and acetic acid (1.43 g, 23.8 mmol) in water (0.9 ml) were stirred during 16 hours at 70° C. (pH of the reaction medium was around 2.0). At the end of the reaction the reaction mixture was concentrated under reduced pressure giving 2.1 g of the crude 3,4-dihydroxyhexane-2,5-dione (56% purity measured by GC vs. internal standard). Crude 3,4-dihydroxyhexane-2,5-dione was distilled under reduced pressure to give 3,4-dihydroxyhexane-2,5-dione (1.56 g, 74% purity, 66% yield) as a pale yellow solid. The product obtained had the same 1H-NMR spectra as those described in Büchi et al, J. Org. Chem., 1973, 38, 123.

Workup

  1. customAt the end of the reaction the reaction mixture
  2. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-b4227e7c66404e609233ed2a0157ab3c
Source dataset
uspto-grants-2012_03
Patent number
US08129570B2

Reaction notes

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