2',6'-Dihydroxyacetophenone → 6'-Hydroxy-2'-(tetrahydropyran-2-yloxy)acetophenone

HRID 230919

Reaktionsgleichung

Reaktionsgleichung von HRID 230919
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[C:3]=1[C:9](=[O:11])[CH3:10].[OH2:12].[C:13]1(C)C=[CH:17][C:16](S(O)(=O)=O)=[CH:15][CH:14]=1>O1CCOCC1.O1C=CCCC1.C(OCC)C>[OH:1][C:2]1[C:3]([C:9](=[O:11])[CH3:10])=[C:4]([O:8][CH:17]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)[CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 2

HCID 696872',6'-DihydroxyacetophenoneHCID 521998p-Toluenesulfonic acid monohydrate

Produkt 1

HCID 113567996'-Hydroxy-2'-(tetrahydropyran-2-yloxy)acetophenoneAusbeute 2.162,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 80803,4-dihydro-2H-pyranLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

2′,6′-Dihydroxyacetophenone (5.0 g) was dissolved in dioxane (20 mL) and 3,4-dihydro-2H-pyran (16 mL). To the solution was added p-toluenesulfonic acid monohydrate (0.21 g), and the mixture was stirred at room temperature for 1.5 hours. The reaction mixture was diluted with diethyl ether, and the mixture was washed with 5% aqueous potassium carbonate solution. The organic layer was extracted with 2 mol/L aqueous sodium hydroxide solution, and the aqueous layer was neutralized until pH was about 8. The resulting mixture was extracted with diethyl ether. The organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate to give the title compound (5.64 g).

Aufarbeitung

  1. washthe mixture was washed with 5% aqueous potassium carbonate solution
  2. extractionThe organic layer was extracted with 2 mol/L aqueous sodium hydroxide solution
  3. extractionThe resulting mixture was extracted with diethyl ether
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate

Quellen und Nachweise

ORD-Eintrag
ord-1df02b8e5f4241548e4ca6542d9a9fd7
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07566699B2

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