Hydrochloric Acid → 6-Methylkojic acid

HRID 1461233Notes

Reaction equation

HRID 1461233 reaction equation
[OH:1][CH2:2][C:3]1[O:4][C:5]([CH2:11]O)=[C:6]([OH:10])[C:7](=[O:9])[CH:8]=1.Cl>[Zn].O>[CH3:11][C:5]1[O:4][C:3]([CH2:2][OH:1])=[CH:8][C:7](=[O:9])[C:6]=1[OH:10]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 27476913-Hydroxy-2,6-bis(hydroxymethyl)-4-pyrone

Product 1

HCID 973716-Methylkojic acid

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

2,6-Dihydroxymethyl-5-hydroxy-4-pyrone, 10 g, was added to 50 ml of water to dissolve at 70° C. To the solution was added 8 g of zinc powders and, 28 ml of conc. hydrochloric acid (12 N) was dropwise added to the mixture over an hour. The mixture was stirred at the same temperature for 30 minutes. Insoluble matters (zinc powders) were removed and the reaction solution was cooled to 5° C. After adjusting its pH to 2 with 50% aqueous sodium hydroxide solution, the mixture was stirred at the same temperature for an hour and the resulting crystals were taken out by filtration, washed with a small quantity of chilled water and dried to give 5.15 g of the title compound.

Workup

  1. dissolutionto dissolve at 70° C
  2. additionwas dropwise added to the mixture over an hour
  3. customwere removed
  4. stirringthe mixture was stirred at the same temperature for an hour
  5. filtrationthe resulting crystals were taken out by filtration
  6. washwashed with a small quantity of chilled water
  7. customdried

Sources & evidence

ORD record
ord-0b5fad01d46d45428e73100348e04d5f
Source dataset
uspto-grants-1991_12
Patent number
US05075299

Reaction notes

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