Kojic Acid → 5-(benzyloxy)-2-(hydroxymethyl)-4H-pyran-4-one

HRID 247168

Reaction equation

HRID 247168 reaction equation
[CH:1]1[C:6](=[O:7])[C:5]([OH:8])=[CH:4][O:3][C:2]=1[CH2:9][OH:10].[OH-].[Na+].[CH2:13](Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CO.O>[CH2:13]([O:8][C:5]1[C:6](=[O:7])[CH:1]=[C:2]([CH2:9][OH:10])[O:3][CH:4]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 3840Kojic AcidHCID 7503Benzyl ChlorideHCID 14798Sodium Hydroxide

Product 1

HCID 9015985-(benzyloxy)-2-(hydroxymethyl)-4H-pyran-4-one

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To a stirred solution of 17 g (0.12 mole) of kojic acid and 5.1 g (0.13 mole) of sodium hydroxide in 190 ml of 10:1 (by volume) methanol-water was added dropwise 17.5 g (0.14 mole) of benzyl chloride. After 4.5 hours at reflux, the mixture was allowed to cool and was poured into 200 ml of ice-water. The resultant solid was collected, washed with water, and dried, giving 22.4 g of analytically pure title compound, m.p. 128°-130°.

Workup

  1. temperatureAfter 4.5 hours at reflux
  2. temperatureto cool
  3. customThe resultant solid was collected
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-332fa967a5b1494198ad8a61e36c51af
Source dataset
uspto-grants-1987_11
Patent number
US04705871

Linked notes

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