Sulfuric Acid → 1-(4-Methoxyphenyl)butane-1,3-dione

HRID 221848

Reaktionsgleichung

Reaktionsgleichung von HRID 221848
[C:1](OCC)(=[O:3])[CH3:2].[H-].[Na+].[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:19])[CH3:18])=[CH:13][CH:12]=1.S(=O)(=O)(O)O>C1COCC1.C(O)C.C1OCCOCCOCCOCCOCCOC1>[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:19])[CH2:18][C:1](=[O:3])[CH3:2])=[CH:13][CH:12]=1

Komponenten

8

Edukt 4

HCID 1118Sulfuric AcidHCID 74764'-MethoxyacetophenoneHCID 8857Ethyl AcetateHCID 24758Sodium hydride

Produkt 1

HCID 776401-(4-Methoxyphenyl)butane-1,3-dioneAusbeute 60,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolKatalysatorHCID 2855718-Crown-6KatalysatorHCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To 9.80 mL of ethyl acetate (100 mmol) in 40 mL dry THF at room temperature was added 2.0 g of 60% sodium hydride (49.9 mmol), 7.50 g of 4′-methoxyacetophenone (49.9 mmol), 100.0 mg of 18-crown-6 (0.40 mmol), and 2 drops of ethanol. After 30 minutes, the reaction was refluxed for 1 h, and then 100 mL of dry THF was added. After an additional 1 h, 30 mL THF was added. After 1 h the reaction was cooled to 0° C. and 25 mL of 10% aqueous sulfuric acid was added. The product was extracted with diethyl ether. The ether extracts were dried with Na2SO4, filtered, and concentrated in vacuo. The crude material was purified via silica gel chromatography eluting with 4:1 hexane:ethyl acetate to give 5.8 g of 1-(4-methoxyphenyl)butane-1,3-dione containing 30% starting material (via 1H NMR 42% yield).

Aufarbeitung

  1. temperaturethe reaction was refluxed for 1 h
  2. waitAfter an additional 1 h
  3. extractionThe product was extracted with diethyl ether
  4. dry with materialThe ether extracts were dried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified via silica gel chromatography
  8. washeluting with 4:1 hexane

Quellen und Nachweise

ORD-Eintrag
ord-8c7ebcd2583645af97db7647fa4bff5c
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207168B2

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