Sulfuric Acid → 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-].[K+].S(=O)(=O)(O)O>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
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To 200 ml of acetone were added 10.0 g of L-sorbose, 166 mg of potassium iodide and 152 mg of conc. sulfuric acid 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 6.79 g (47.0%) of 2,3:4,6-di-O-isopropylidene-L-sorbofuranose (purity ≥96%).
Workup
- temperaturethe mixture was refluxed
- customDuring this reaction
- dry with materialthe refluxing solvent was dried with 20 g of Molecular Sieves 3A
Sources & evidence
- ORD record
- ord-bb176406d6864dd28eacef6e1db8536d
- Source dataset
- uspto-grants-1984_08
- Patent number
- US04464530
Reaction notes
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