Reaction equation
[CH:1]1[C:6](=[O:7])[C:5]([OH:8])=[CH:4][O:3][C:2]=1[CH2:9]O.S(Cl)([Cl:13])=O>CN(C)C=O>[CH:1]1[C:6](=[O:7])[C:5]([OH:8])=[CH:4][O:3][C:2]=1[CH2:9][Cl:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 10 °C
Procedure
50 g(351.8 mmol) of kojic acid was dissolved in 250 ml of N,N-dimethylformamide. The resulting solution was cooled in an ice bath of 10° C. and 30 ml(411.3 mmol) of thionyl chloride was added dropwise thereto. The mixture was stirred at room temperature for 2 hours and 2000 ml of ice water was added. The precipitate was filtered and dissolved into 1000 ml of ethyl acetate. The reaction product was dried over magnesium sulfate, decolored with active charcoal and filtered. The filtrate was concentrated and hexane was added to give crystals, which were then dried under vacuum to give 37.5 g(66.83%) of the desired chlorokojic acid as a yellow solid.
Workup
- filtrationThe precipitate was filtered
- dissolutiondissolved into 1000 ml of ethyl acetate
- dry with materialThe reaction product was dried over magnesium sulfate
- filtrationfiltered
- concentrationThe filtrate was concentrated
- additionhexane was added
- customto give crystals, which
- customwere then dried under vacuum
Sources & evidence
- ORD record
- ord-50edb9407454424e925ab5b76636d490
- Source dataset
- uspto-grants-1996_01
- Patent number
- US05486624
Linked notes
Loading…