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

HRID 746283Notes

Reaction equation

HRID 746283 reaction equation
[CH:1]1[C:6](=[O:7])[C:5]([OH:8])=[CH:4][O:3][C:2]=1[CH2:9][OH:10].O.[OH-].[Na+].[CH2:14](Cl)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CO>[CH2:14]([O:8][C:5]1[C:6](=[O:7])[CH:1]=[C:2]([CH2:9][OH:10])[O:3][CH:4]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3840Kojic AcidHCID 7503Benzyl ChlorideHCID 14798Sodium Hydroxide

Product 1

HCID 9015985-(benzyloxy)-2-(hydroxymethyl)-4H-pyran-4-oneYield 80.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Kojic acid (17.05 g, 0.120 mole) was suspended in methanol (170 ml), H2O (17 ml) and sodium hydroxide (5.14 g, 0.128 mole) added and the mixture allowed to stand. To the resulting solution, benzyl chloride (17.5 g, 0.138 mole) was added dropwise and the solution refluxed for 4.5 h. and cooled. The resulting brown solution was poured into 200 ml H+ /H2O. The precipitate was filtered and stored at 65° C. overnight to give 22.38 g of the title compound as a yellow crystalline solid (m.p. 128°-130° C.).

Workup

  1. temperaturethe solution refluxed for 4.5 h.
  2. temperaturecooled
  3. filtrationThe precipitate was filtered

Sources & evidence

ORD record
ord-3b41203169594429b23c2b1d731be023
Source dataset
uspto-grants-1986_07
Patent number
US04603144

Reaction notes

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