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

HRID 1252590Notes

Reaction equation

HRID 1252590 reaction equation
[Na].[OH:2][C:3]1[C:4](=[O:11])[CH:5]=[C:6]([CH2:9][OH:10])[O:7][CH:8]=1.[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CO>[OH:10][CH2:9][C:6]1[O:7][CH:8]=[C:3]([O:2][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:4](=[O:11])[CH:5]=1

Participants

5

Reactant 3

HCID 3840Kojic AcidHCID 7498Benzyl BromideHCID 5360545Sodium

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
30 °C

Procedure

69 g (3 mol) of sodium were dissolved in 5 1 of methanol. Subsequently 425.3 g (3 mol) of 5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one was added and stirred at 30° C. until a clear solution was obtained. 595 g (3.5 mol) of benzyl bromide was then added and stirred for 1 hour under reflux. The warm and very dark colored solution was poured into 15 1 of ice water. The product crystallized immediately. The crystals were collected and washed first with 8 1 of water and then twice with 2.5 1 of ether. The product was left to stand overnight and finally dried at 50° C. for 16 hrs. Yield: 646 g=92.6%.

Workup

  1. customwas obtained
  2. stirringstirred for 1 hour
  3. temperatureunder reflux
  4. temperatureThe warm
  5. customThe product crystallized immediately
  6. customThe crystals were collected
  7. washwashed first with 8 1 of water
  8. waitThe product was left
  9. customfinally dried at 50° C. for 16 hrs

Sources & evidence

ORD record
ord-96f2b2fa749046978c703de06dd0d15e
Source dataset
uspto-grants-1988_05
Patent number
US04743685

Reaction notes

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