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

HRID 648763Notes

Reaction equation

HRID 648763 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-205a22f7f9894a4e9c4ff7bc4c010b08
Source dataset
uspto-grants-1988_04
Patent number
US04735964

Reaction notes

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