Kojic Acid → Chlorokojic acid

HRID 1846828Notes

Reaction equation

HRID 1846828 reaction equation
[OH:1][C:2]1[C:3](=[O:10])[CH:4]=[C:5]([CH2:8]O)[O:6][CH:7]=1.O=S(Cl)[Cl:13]>ClCCl>[Cl:13][CH2:8][C:5]1[O:6][CH:7]=[C:2]([OH:1])[C:3](=[O:10])[CH:4]=1

Participants

4

Reactant 2

HCID 3840Kojic AcidHCID 24386Thionyl Chloride

Product 1

HCID 82051Chlorokojic acidYield 61.96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5-hydroxy-2-hydroxymethyl-pyran-4-one (1) (100.0 g, 703.68 mmol) in dichloromethane (750 mL) was added SOCl2 (102.0 mL) very slowly and the reaction mixture was stirred at room temperature for 16 h. After completion of the reaction, the solvent was evaporated to remove volatile compounds under reduced pressure to get a crude compound. It was then purified by hexane wash to get 2-chloromethyl-5-hydroxy-pyran-4-one (2) (70.0 g, 61.96%) as an off white solid.

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated
  3. customto remove volatile compounds under reduced pressure
  4. customto get a crude compound
  5. customIt was then purified by hexane
  6. washwash

Sources & evidence

ORD record
ord-f2479d971e144e83840eb9ddb119ff9c
Source dataset
uspto-grants-2015_02
Patent number
US08952039B2

Reaction notes

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