Kojic Acid → Chlorokojic acid

HRID 2280238Notes

Reaction equation

HRID 2280238 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>>[Cl:13][CH2:9][C:2]1[O:3][CH:4]=[C:5]([OH:8])[C:6](=[O:7])[CH:1]=1

Participants

3

Reactant 2

HCID 3840Kojic AcidHCID 24386Thionyl Chloride

Product 1

HCID 82051Chlorokojic acidYield 71%

Procedure

50 g kojic acid (350 mmol, 1 equiv) was added to 220 ml thionyl chloride with stirring. The reaction vessel was cooled with ice and the mixture was stirred for 1 hour until a bright yellow suspension had formed. The mixture was vacuum filtered to give a crude white solid after washing with petroleum spirit. This solid was recrystallised from hot water to give 40 g of off-white crystals in 71% yield.

Workup

  1. temperatureThe reaction vessel was cooled with ice
  2. stirringthe mixture was stirred for 1 hour until a bright yellow suspension
  3. customhad formed
  4. filtrationfiltered
  5. customto give a crude white solid
  6. washafter washing with petroleum spirit
  7. customThis solid was recrystallised from hot water

Sources & evidence

ORD record
ord-d4065aa452604becb49e4672dd8d1acf
Source dataset
uspto-grants-2015_09
Patent number
US09138495B2

Reaction notes

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