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

HRID 1279419Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1279419
[CH:1]1[C:6](=[O:7])[C:5]([OH:8])=[CH:4][O:3][C:2]=1[CH2:9][OH:10].[OH2:11].[CH2:12]=O.Cl>C(O)(C)C>[OH:11][CH2:12][C:4]1[O:3][C:2]([CH2:9][OH:10])=[CH:1][C:6](=[O:7])[C:5]=1[OH:8]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 962WaterHCID 3840Kojic Acid

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

50 g (0.35 mol) of kojic acid (1) was added to 200 ml of water and the pH of the solution was adjusted to 8.5 using 50% aqueous sodium hydroxides. 37% Formaldehyde (30 ml) was added and the solution allowed stirring 12 hrs. The reaction mixture was acidified to pH 1 with 37% hydrochloric acid and concentrated in vacuo to dryness. The residue was extracted with 2×200 ml of isopropanol at 90° C. The isopropanol extracts were combined and concentrated to yield the crude product (2) (55.4 g, 92%). Recrystallisauon from isopropanol afforded the analytically pure compound as colourless needles. m.p. 160-161° C.

Aufarbeitung

  1. concentrationconcentrated in vacuo to dryness
  2. extractionThe residue was extracted with 2×200 ml of isopropanol at 90° C
  3. concentrationconcentrated
  4. customto yield the crude product (2) (55.4 g, 92%)

Quellen und Nachweise

ORD-Eintrag
ord-9a484065b0f040cea5fcf42d6f8b97f0
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06448273B1

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