(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal → Sorbitol

HRID 850948Notes

Reaction equation

HRID 850948 reaction equation
[O:1]=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].[H][H]>[Ni]>[OH:12][CH2:11][C@@H:9]([C@H:7]([C@@H:5]([C@@H:3]([CH2:2][OH:1])[OH:4])[OH:6])[OH:8])[OH:10].[CH2:11]([OH:12])[C@H:9]([C@H:7]([C@@H:5]([C@@H:3]([CH2:2][OH:1])[OH:4])[OH:6])[OH:8])[OH:10]

Participants

5

Reactant 2

HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal2×HCID 178418361HCID 178418361, compound

Product 2

HCID 5780SorbitolHCID 6251Mannitol

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

A mixture of 60 ml of a 45 percent aqueous solution of glucose containing 6 g of a 10 percent nickel on titanium dioxide catalyst, reduced at 250° C., was reacted with hydrogen at 700 psig and 120° C. for 5 hours. The cooled reaction mixture was then analyzed by high pressure liquid chromatography which showed that 98 percent of the glucose had reacted to afford as the only two products sorbitol and mannitol with selectivity of 95 percent and 3 percent respectively.

Workup

  1. customreduced at 250° C.
  2. customThe cooled reaction mixture
  3. customhad reacted

Sources & evidence

ORD record
ord-7b3d9a1572da4f0da0b02993e4472d37
Source dataset
uspto-grants-1983_05
Patent number
US04382150

Reaction notes

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