Phosphoric Acid → Diacetone-D-glucose

HRID 2051670Notes

Reaction equation

HRID 2051670 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].P(=O)(O)(O)O.[OH-].[Na+]>CC(C)=O.[Cl-].[Zn+2].[Cl-]>[CH3:2][C:3]1([CH3:5])[O:4][C@@H:3]([C@H:5]2[O:6][C@@H:11]3[O:12][C:9]([CH3:11])([CH3:7])[O:10][C@@H:9]3[C@H:7]2[OH:8])[CH2:2][O:1]1

Participants

6

Reactant 3

HCID 1004Phosphoric AcidHCID 14798Sodium HydroxideHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Product 1

HCID 7067560Diacetone-D-glucoseYield 91%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 180AcetoneSolvent

Procedure

To a suspension of 100 grams of anhydrous D-glucose in one liter of anhydrous acetone is added 80 grams of anhydrous zinc chloride and 5 grams of 85% phosphoric acid. The mixture is stirred for 30 hours at room temperature and then neutralized with a 50% NaOH solution. The insoluble materials are removed by filtration and washed with acetone. The combined filtrates are evaporated under reduced pressure to heavy syrup and the residual syrup is diluted with 500 ml. of chloroform. The chloroform solution is extracted three times with water and concentrated in vacuo to give crude 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose. The crude product is purified by crystallization from a chloroform and hexane mixture to give 77 grams (91% yield based on the D-glucose consumed) of a pure product having a melting point of 105°-109° C.

Workup

  1. customThe insoluble materials are removed by filtration
  2. washwashed with acetone
  3. customThe combined filtrates are evaporated under reduced pressure to heavy syrup
  4. additionthe residual syrup is diluted with 500 ml
  5. extractionThe chloroform solution is extracted three times with water
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c6cadff03d794f249ac692b5a556b9a1
Source dataset
uspto-grants-1980_01
Patent number
US04181795

Reaction notes

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