Kojic Acid → 4H-Pyran-4-one, 2-(hydroxymethyl)-5-[(4-methoxyphenyl)methoxy]-

HRID 1086178Notes

Reaction equation

HRID 1086178 reaction equation
[CH:1]1[C:6](=[O:7])[C:5]([OH:8])=[CH:4][O:3][C:2]=1[CH2:9][OH:10].C(=O)([O-])[O-].[K+].[K+].[CH3:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Cl)=[CH:21][CH:20]=1>>[CH3:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][O:8][C:5]2[C:6](=[O:7])[CH:1]=[C:2]([CH2:9][OH:10])[O:3][CH:4]=2)=[CH:21][CH:20]=1

Participants

4

Reactant 3

HCID 3840Kojic AcidHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 104916984H-Pyran-4-one, 2-(hydroxymethyl)-5-[(4-methoxyphenyl)methoxy]-

Procedure

42.6 9 of kojic acid is dissolved in 350 ml of N-dimethylformamide, then 82.8 g of anhydrous potassium carbonate and 55 g of p-methoxybenzyl chloride are added thereto, and reacted at 70°-75° C. for 1.5 hours. After the reaction, the reaction mixture is concentrated to about half the volume, and added dropwise to 700 ml of water with ice cooling. The formed precipitates are filtered off, washed with water and ethyl acetate and dried to obtain 59.9 g of 5-p-methoxybenzyloxy-2-hydroxymethyl-4-pyrone.

Workup

  1. customreacted at 70°-75° C. for 1.5 hours
  2. customAfter the reaction
  3. concentrationthe reaction mixture is concentrated to about half the volume
  4. additionadded dropwise to 700 ml of water with ice cooling
  5. customThe formed precipitates
  6. filtrationare filtered off
  7. washwashed with water and ethyl acetate
  8. customdried

Sources & evidence

ORD record
ord-eecb62fdb5bb4f9aabc18e7cb58e5848
Source dataset
uspto-grants-1991_07
Patent number
US05028601

Reaction notes

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