Water → 3-butoxy-6-hydroxy-9H-xanthen-9-one

HRID 54717

Reaktionsgleichung

Reaktionsgleichung von HRID 54717
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:17])[C:7]3[C:12]([O:13][C:14]=2[CH:15]=1)=[CH:11][C:10]([OH:16])=[CH:9][CH:8]=3.O.[CH2:19](Br)[CH2:20][CH2:21][CH3:22]>C(O)(C)C>[CH2:19]([O:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:17])[C:7]3[C:12]([O:13][C:14]=2[CH:15]=1)=[CH:11][C:10]([OH:16])=[CH:9][CH:8]=3)[CH2:20][CH2:21][CH3:22]

Komponenten

5

Edukt 3

HCID 962WaterHCID 8002Butyl bromideHCID 57493223,6-dihydroxy-9H-xanthen-9-one2×

Produkt 1

HCID 199597283-butoxy-6-hydroxy-9H-xanthen-9-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

3,6-Dihydroxy xanthone (1,60.7 mmol) was dissolved into hot basic water (Na2CO3 240 mmol in 600 ml water). After the 3,6-dihydroxy xanthone was completely dissolved, the temperature was controlled to 70° C. Isopropyl alcohol (10 ml) was added to the reaction mixture and butyl bromide (180 mmol) was added dropwise. The reaction mixture was stirred rigorously for 72 hours. A white precipitate appeared which was then filtered and washed with water. There was almost no disubstituted compound in the product. This precipitate was dissolved in 3% NaOH, filtered and finally reprecipitated with HCl yielding 90% of 3-butoxy-6-hydroxy xanthone.

Aufarbeitung

  1. customwas controlled to 70° C
  2. additionwas added dropwise
  3. filtrationwas then filtered
  4. washwashed with water
  5. dissolutionThis precipitate was dissolved in 3% NaOH
  6. filtrationfiltered
  7. customfinally reprecipitated with HCl yielding 90% of 3-butoxy-6-hydroxy xanthone

Quellen und Nachweise

ORD-Eintrag
ord-6e93286652fb432280b5722491b4ec1d
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05623080

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