Sulfuric Acid → Diacetone-D-glucose

HRID 1374785Notes

Reaction equation

HRID 1374785 reaction equation
S(=O)(=O)(O)O.[OH:6][C@H:7]1[O:15][C@H:14]([CH2:16][OH:17])[C@@H:12]([OH:13])[C@H:10]([OH:11])[C@H:8]1[OH:9].[OH-].[Na+]>CC(C)=O>[CH3:7][C:8]1([CH3:10])[O:13][C@@H:12]([C@H:14]2[O:15][C@@H:7]3[O:6][C:14]([CH3:16])([CH3:12])[O:9][C@@H:8]3[C@H:16]2[OH:17])[CH2:10][O:11]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 79025Alpha-D-Glucose

Product 1

HCID 7067560Diacetone-D-glucoseYield 112.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Sulfuric acid (40 ml) is added dropwise to a solution of α-D-glucose (41) (50 g. 0.28 mol) in acetone (1 l) at 0° C. The reaction mixture is stirred for 24 h and then it is neutralized using sodium hydroxide (6 M). The acetone is evaporated and the aqueous layer is extracted with chloroform (×2). The chloroform is dried (MgSO4) filtered and evaporated. Crystallization from cyclohexane yielded the di-isopropylidene glucose (42) (41 g. 57%).

Workup

  1. customThe acetone is evaporated
  2. extractionthe aqueous layer is extracted with chloroform (×2)
  3. dry with materialThe chloroform is dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customCrystallization from cyclohexane

Sources & evidence

ORD record
ord-d06d45a843704ab387c09b74986eba1c
Source dataset
uspto-grants-2007_01
Patent number
US07166611B2

Reaction notes

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