Kojic Acid → 5-Hydroxy-2-{[(oxan-2-yl)oxy]methyl}-4H-pyran-4-one

HRID 1804723Notes

Reaction equation

HRID 1804723 reaction equation
[CH:1]1[C:6](=[O:7])[C:5]([OH:8])=[CH:4][O:3][C:2]=1[CH2:9][OH:10].[OH2:11].[C:12]1(C)C=[CH:16][C:15](S(O)(=O)=O)=[CH:14][CH:13]=1.[OH-].[Na+]>O1CCCC1.O1C=CCCC1>[OH:8][C:5]1[C:6](=[O:7])[CH:1]=[C:2]([CH2:9][O:10][CH:16]2[CH2:15][CH2:14][CH2:13][CH2:12][O:11]2)[O:3][CH:4]=1

Participants

6

Reactant 3

HCID 3840Kojic AcidHCID 14798Sodium HydroxideHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 137117895-Hydroxy-2-{[(oxan-2-yl)oxy]methyl}-4H-pyran-4-oneYield 29,265.199%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 80803,4-dihydro-2H-pyranSolvent

Procedure

To a suspension of 14.3 g of kojic acid in 57 mL of tetrahydrofuran, 11 mL of 3,4-dihydro-2H-pyran and 77 mg of p-toluenesulfonic acid monohydrate were added, and the mixture was stirred for 6 hours at room temperature. To the mixture, 1 mL of a 0.5 mol/L sodium hydroxide aqueous solution was added, and the solvent was evaporated under reduced pressure to give 26.8 g of 5-hydroxy-2-((tetrahydro-2H-pyran-2-yloxy)methyl)-4H-pyran-4-one as a light yellow solid.

Workup

  1. additionwere added
  2. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-795ea3a9880f4007aa6b25dec1c8c733
Source dataset
uspto-grants-2013_01
Patent number
US08354426B2

Reaction notes

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