Sulfuric Acid → Diacetone-D-glucose

HRID 843209

Reaction equation

HRID 843209 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 (X2). 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 (X2)
  3. dry with materialThe chloroform is dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customCrystallization from cyclohexane

Sources & evidence

ORD record
ord-80b91a09cd0a4ad6b1d6e94c624dd2c4
Source dataset
uspto-grants-2002_04
Patent number
US06376657B1

Linked notes

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