Formaldehyde → 3-Hydroxy-2,6-bis(hydroxymethyl)-4-pyrone

HRID 1461232Notes

Reaction equation

HRID 1461232 reaction equation
[CH:1]1[C:6](=[O:7])[C:5]([OH:8])=[CH:4][O:3][C:2]=1[CH2:9][OH:10].[OH-:11].[Na+].[CH2:13]=O.S(=O)(=O)(O)O>O>[OH:10][CH2:9][C:2]1[O:3][C:4]([CH2:13][OH:11])=[C:5]([OH:8])[C:6](=[O:7])[CH:1]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 3840Kojic AcidHCID 14798Sodium Hydroxide

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Kojic acid, 28 g, was suspended in 100 ml of water and a pH of the suspension was adjusted to 10.5 with 50% sodium hydroxide. After 16 ml of 35% formalin was added to the suspension, the mixture was stirred at room temperature for 3 hours. After completion of the reaction, the reaction mixture was cooled to 5° C. and its pH was adjusted to 2.0 with 50% sulfuric acid. Then, the reaction solution was concentrated to about 50 ml and the resulting crystals were taken out by filtration, washed with a small quantity of chilled water and dried to give 28 g of the title compound.

Workup

  1. customAfter completion of the reaction
  2. temperaturethe reaction mixture was cooled to 5° C.
  3. concentrationThen, the reaction solution was concentrated to about 50 ml
  4. filtrationthe resulting crystals were taken out by filtration
  5. washwashed with a small quantity of chilled water
  6. customdried

Sources & evidence

ORD record
ord-3b1c6ca51917431aab56bd04c1e6380a
Source dataset
uspto-grants-1991_12
Patent number
US05075299

Reaction notes

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