Sulfuric Acid → Diacetone-D-glucose
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]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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%).