L-(-)-Sorbose → Diacetone L-sorbose
Reaction equation
[OH:1][CH2:2][C:3]([C@H:5]([C@@H:7]([C@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])=[O:4].I(Cl)(Cl)Cl>CC(C)=O>[CH3:2][C:3]1([CH3:5])[O:6][C@H:5]2[C@@H:7]3[O:8][C:9]([CH3:11])([CH3:7])[O:10][C@:9]3([CH2:11][OH:12])[O:4][C@H:3]2[CH2:2][O:1]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To 200 ml of acetone were added 10.0 g of L-sorbose and 234 mg of iodine trichloride and the mixture was refluxed with stirring in a water bath at 60° C. for 4 hours. During this reaction, the refluxing solvent was dried with 20 g of Molecular Sieves 3A interposed between the reaction vessel and the cooling jacket. The reaction mixture was then subjected to an after-treatment similar to that described in Example 11 to give 9.85 g (68.2%) of 2,3:4,6-di-O-isopropylidene-L-sorbofuranose (purity ≥98%).