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

HRID 881792Notes

Reaction equation

HRID 881792 reaction equation
Cl[O-:2].[Na+].[Cl+].Cl[O-].[O:7]=[CH:8][C@@H:9]([C@H:11]([C@@H:13]([C@@H:15]([CH2:17][OH:18])[OH:16])[OH:14])[OH:12])[OH:10]>>[O:7]=[CH:8][C@@H:9]([C@H:11]([C@@H:13]([C@@H:15]([CH2:17][OH:18])[OH:16])[OH:14])[OH:12])[OH:10].[O:7]=[C:8]([OH:2])[C@@H:9]([C@H:11]([C@@H:13]([C@@H:15]([CH2:17][OH:18])[OH:16])[OH:14])[OH:12])[OH:10]

Participants

4

Reactant 2

HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 178479012HCID 178479012, compound

Product 2

HCID 10690Gluconic AcidHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Procedure

Over two hours, 164 g. of 12% active chlorine sodium hypochlorite solution are added, a quantity corresponding with a molar weight 1:1 with respect to the glucose, by maintaining the pH value between 7.0 and 9.0 and, at the end of the addition, the stirring is continued for other 30 minutes. The control of the accomplished execution is carried out through HPLC or through polarimetric readings. The oxidation of glucose to gluconic acid is obtained, as it can be verified by the 13C NMR spectrum depicted in FIG. 1.

Workup

  1. additionat the end of the addition
  2. waitthe stirring is continued for other 30 minutes

Sources & evidence

ORD record
ord-aaccc88b3b534017ac4544045f02309d
Source dataset
uspto-grants-2015_03
Patent number
US08993748B2

Reaction notes

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