Formaldehyde → 3-hydroxy-2-(hydroxymethyl)-6-methyl-4H-pyran-4-one

HRID 1461242Notes

Reaction equation

HRID 1461242 reaction equation
[OH:1][C:2]1[C:3](=[O:9])[CH:4]=[C:5]([CH3:8])[O:6][CH:7]=1.[OH-:10].[Na+].[CH2:12]=O.S(=O)(=O)(O)O>O>[OH:10][CH2:12][C:7]1[O:6][C:5]([CH3:8])=[CH:4][C:3](=[O:9])[C:2]=1[OH:1]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 695214H-Pyran-4-one, 5-hydroxy-2-methyl-

Product 1

HCID 105110973-hydroxy-2-(hydroxymethyl)-6-methyl-4H-pyran-4-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-Hydroxy-2-methyl-4-pyrone, 6 g, was suspended in 25 ml of water and a pH of the suspension was adjusted to 10.5 with 50% sodium hydroxide. After 5 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 half and the resulting crystals were taken out by filtration and washed with a small quantity of chilled water to give 5.9 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 half
  4. filtrationthe resulting crystals were taken out by filtration
  5. washwashed with a small quantity of chilled water

Sources & evidence

ORD record
ord-a9cfc5c9fa46458ea23c770499bea5ae
Source dataset
uspto-grants-1991_12
Patent number
US05075299

Reaction notes

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