Methylglyoxal → 1,6-Dideoxyhexo-2,5-diulose

HRID 2252389Notes

Reaction equation

HRID 2252389 reaction equation
[CH3:1][C:2]([CH:4]=[O:5])=[O:3].[OH2:6].O[CH2:8][C:9](=[O:11])[CH3:10]>C(OCC)(=O)C.C([O-])(=O)C.[Zn+2].C([O-])(=O)C>[OH:6][CH:8]([CH:4]([OH:5])[C:2](=[O:3])[CH3:1])[C:9](=[O:11])[CH3:10]

Participants

6

Reactant 3

HCID 880MethylglyoxalHCID 962WaterHCID 8299Hydroxyacetone

Product 1

HCID 780331,6-Dideoxyhexo-2,5-diulose

Reagents, catalysts & solvents 2

HCID 11192Zinc AcetateCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl glyoxal 40% wt in water (9 g, 50 mmoles), zinc acetate (0.44 g) and hydroxy-acetone (7.4 g) in ethyl acetate (20 ml) were stirred during 40 h at 38/40° (pH of the reaction medium was around 4.5). At the end of the reaction (which can be checked by gas chromatography), the reaction mixture was extracted with ethyl acetate (3×50 ml). The organic phase was washed to neutral with brine (1×), dried over magnesium sulphate and concentrated under vacuum giving 6 g of the crude 3,4-dihydroxyhexane-2,5-dione who was Bulb-to-bulb distilled at 0.1 mbar and 120-150° to obtain 3.8 g of a mixture of the two 3,4-dihydroxyhexane-2,5-dione isomers.

Workup

  1. customAt the end of the reaction (which can be checked by gas chromatography)
  2. extractionthe reaction mixture was extracted with ethyl acetate (3×50 ml)
  3. washThe organic phase was washed to neutral with brine (1×)
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-7cc9ccdfd28c49958a4d2086d3b42abb
Source dataset
uspto-grants-2008_01
Patent number
US07321067B2

Reaction notes

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