Hydrochloric Acid → 7-hydroxy-2-(hydroxymethyl)-chromen-4-one

HRID 635223Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 635223
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:17])[CH:7]=[C:8]([C:12](OCC)=[O:13])[O:9]2)=[CH:4][CH:3]=1.[Cl-].[Ca+2].[Cl-].[BH4-].[Na+].Cl>C(O)C.O>[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:17])[CH:7]=[C:8]([CH2:12][OH:13])[O:9]2)=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydride2×HCID 5284359Calcium ChlorideHCID 5376802ethyl 7-hydroxy-4-oxo-4H-chromen-2-carboxylate

Produkt 1

HCID 105119297-hydroxy-2-(hydroxymethyl)-chromen-4-oneAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a suspension of 5 g (21 mmoles) of ethyl 7-hydroxy-4-oxo-chromen-2-carboxylate and 5 g (45 mmoles) of anhydrous calcium chloride in 100 mL of absolute ethanol, cooled at 0° C., were added 3 g of sodium borohydride in several portions and the mixture was stirred at room temperature for 16 hours. Further 1 g of sodium borohydride was added and stirred for an additional 2 hours. The reaction mixture was suspended in 200 mL of water and acidified slowly with HCl. The precipitate was filtered, washed with water and dried at vaccum to give 2.7 g de 7-hydroxy-2-(hydroxymethyl)-chromen-4-one as a solid, yield 66%, mp 250-252° C.

Aufarbeitung

  1. stirringstirred for an additional 2 hours
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. customdried at vaccum

Quellen und Nachweise

ORD-Eintrag
ord-6c5b322ea8f54b968525a0ef69da2925
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06187793B1

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