Hydrochloric Acid → 1-Hydroxy-3-phenylmethoxyxanthen-9-one

HRID 83098

Reaktionsgleichung

Reaktionsgleichung von HRID 83098
[OH:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[O:7][C:6]=2[CH:5]=[C:4]([OH:17])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.Cl>O.CC(C)=O>[CH2:24]([O:17][C:4]1[CH:3]=[C:2]([OH:1])[C:15]2[C:14](=[O:16])[C:13]3[C:8]([O:7][C:6]=2[CH:5]=1)=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 54881931,3-Dihydroxy-xanthone

Produkt 1

HCID 57412951-Hydroxy-3-phenylmethoxyxanthen-9-oneAusbeute 42,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

The compound (1.77 g, 7.75 mmol) synthesized in Step 1 of Example 2 and K2CO3 (2.76 g, 0.02 mol) were charged to a dry round-bottom flask, and anhydrous acetone (200 mL) was added thereto. To the reaction mixture was added benzyl bromide (1.38 mL, 11.63 mmol), followed by stirring under reflux at 60° C. for one day. After the reaction was completed, the reaction liquid was cooled to room temperature, and 200 mL of water was added thereto. The reaction liquid was acidified with 3M-HCl and extracted twice with ethyl acetate. The organic layer was combined, successively washed with water and brine, and then dried over anhydrous Na2SO4. The solvent was removed under reduced pressure. The resulting residue was separated and purified by silica gel column chromatography (developing solvent: CH2Cl2) to give the title compound (1.05 g, 42.6%) as a light yellow solid.

Aufarbeitung

  1. customthe reaction liquid
  2. temperaturewas cooled to room temperature
  3. customThe reaction liquid
  4. extractionextracted twice with ethyl acetate
  5. washsuccessively washed with water and brine
  6. dry with materialdried over anhydrous Na2SO4
  7. customThe solvent was removed under reduced pressure
  8. customThe resulting residue was separated
  9. custompurified by silica gel column chromatography (developing solvent: CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-f743684ac5604071bf5504ab69ea08ef
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846749B2

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