Sodium Carbonate → 2-keto-D-Gluconic acid

HRID 971388Notes

Reaction equation

HRID 971388 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[BH4-].[Na+].[CH2:9]([OH:21])[CH:10]([OH:20])[CH:11]([OH:19])[CH:12]([OH:18])[C:13]([C:15]([O-:17])=[O:16])=[O:14].[Na+]>CO>[CH2:9]([OH:21])[C@@H:10]([OH:20])[C@@H:11]([OH:19])[C@H:12]([OH:18])[C:13]([C:15]([OH:17])=[O:16])=[O:14]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 4311764Sodium borohydrideHCID 23686669xylo-2-Hexulosonic acid, sodium salt (1:1)

Product 1

HCID 30354562-keto-D-Gluconic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A 10% aqueous solution of sodium 2,5-diketogluconate was adjusted to a pH of 6.1 by addition of sodium carbonate, methanol was added to give 50% by volume and the solution was cooled to between -15° C. and -25° C. One equivalent of sodium borohydride was added to the cooled solution which was stirred for six hours at -15° C. to -25° C. and at room temperature overnight. A mixture of sodium 2-ketogulonate and 2-ketogluconate was isolated by precipitation with methanol and filtration. Analysis of the methyl esters by liquid chromotography showed a 78:22 ratio of 2-ketogulonic acid to 2-ketogluconic acid in the product mixture.

Workup

  1. additionwas added
  2. customto give 50% by volume
  3. temperaturethe solution was cooled to between -15° C. and -25° C

Sources & evidence

ORD record
ord-e430dc9b332e4d718c24bf59485a8c5e
Source dataset
uspto-grants-1979_07
Patent number
US04159990

Reaction notes

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