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

HRID 1866115Notes

Reaction equation

HRID 1866115 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.Cl>O>[OH:8][C:5]1[C:6](=[O:7])[CH:1]=[C:2]([CH2:9][OH:10])[O:3][C:4]=1[CH2:13][OH:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712Formaldehyde2×HCID 3840Kojic AcidHCID 14798Sodium Hydroxide

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

In a 100 mL round bottom flask were added Kojic acid (FLUKA, 5 g), 1N NaOH (39 mL) and H2O (10 mL). The mixture was cooled (ice/water bath) and 37% aqueous formaldehyde (ALDRICH, 2.9 mL) was added dropwise. After 34 h at room temperature aditional 37% aqueous formaldehyde (ALDRICH, 0.5 mL) was added dropwise and the solution allowed to stir for 18 h. The mixture was acidified by adding concentrated HCl, and the solvent eliminated to dryness under vacuum to give a crude product which was treated with chilled water to afford a solid precipitated which was filtered and vacuum dried. 3.056 g of the title compound were obtained as a white solid. The filtrate was concentrated under vacuum and a second crop of solid separated. An additional 1.154 g of the title compound were obtained.

Workup

  1. additionwas added dropwise
  2. customto give a crude product which
  3. customto afford a solid
  4. customprecipitated which
  5. filtrationwas filtered
  6. customvacuum dried

Sources & evidence

ORD record
ord-c839db8876d444e592323a90fd112ab3
Source dataset
uspto-grants-2009_12
Patent number
US07629365B2

Reaction notes

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