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

HRID 1252638Notes

Reaction equation

HRID 1252638 reaction equation
[OH:1][C:2]1[C:3](=[O:10])[CH:4]=[C:5]([CH2:8][OH:9])[O:6][CH:7]=1.[OH-].[Na+].[CH2:13](Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CO.O>[OH:9][CH2:8][C:5]1[O:6][CH:7]=[C:2]([O:1][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:3](=[O:10])[CH:4]=1

Participants

6

Reactant 3

HCID 3840Kojic AcidHCID 7503Benzyl ChlorideHCID 14798Sodium Hydroxide

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

A suspension of 5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one (56.8 g, 0.4 mole) in 400 ml of methanol was treated with sodium hydroxide, (16 g, 0.4 mole) in 200 ml of warm methanol followed by 50.6 g (46 ml, 0.4 mole) of benzyl chloride. The mixture was heated to reflux for 3.5 hours, cooled, and poured in 1 L of water. The resulting solid was filtered and washed with ca. 1.5 L of water, 200 ml of ethanol and 400 ml of hexane. After drying under high vacuum, the weight of product was 55.7 g.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3.5 hours
  3. temperaturecooled
  4. filtrationThe resulting solid was filtered
  5. washwashed with ca. 1.5 L of water, 200 ml of ethanol and 400 ml of hexane
  6. customAfter drying under high vacuum

Sources & evidence

ORD record
ord-113adf3f884048f3af93323873c16f65
Source dataset
uspto-grants-1988_05
Patent number
US04743685

Reaction notes

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