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

HRID 253407

Reaction equation

HRID 253407 reaction equation
[CH:1]1[C:6](=[O:7])[C:5]([OH:8])=[CH:4][O:3][C:2]=1[CH2:9][OH:10].[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16]Br)=[CH:14][CH:13]=1.[OH-].[Na+]>CO.O>[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][O:8][C:5]2[C:6](=[O:7])[CH:1]=[C:2]([CH2:9][OH:10])[O:3][CH:4]=2)=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 3840Kojic AcidHCID 14798Sodium HydroxideHCID 693291-(Bromomethyl)-4-chlorobenzene

Product 1

HCID 580868345-(4-Chloro-benzyloxy)-2-hydroxymethyl-pyran-4-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Kojic acid (70, 5.00 g, 35.2 mmol) and 4-chlorobenzyl bromide (22, 7.95 g, 38.7 mmol) were suspended in methanol (40 mL) in an 80 mL sealed tube. Sodium hydroxide in water (12 M, 2.93 ml) was added, The reaction was heated at 80° C. overnight. The resulting suspension was concentrated. Water was added and the mixture was filtered and washed with water to provide a brown solid. Washing with minimal methanol on the filter removed the brown color. A white solid (71, 7.58 g, 80%) was isolated. 1H-NMR was consistent with the desired compound.

Workup

  1. customsealed tube
  2. concentrationThe resulting suspension was concentrated
  3. additionWater was added
  4. filtrationthe mixture was filtered
  5. washwashed with water
  6. customto provide a brown solid
  7. washWashing with minimal methanol on the filter
  8. customremoved the brown color
  9. customA white solid (71, 7.58 g, 80%) was isolated

Sources & evidence

ORD record
ord-f4a65107e2984098a7215a47509e8780
Source dataset
uspto-grants-2011_01
Patent number
US07872018B2

Linked notes

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