Acetyl chloride → Ethyl 6-acetyl-1,4-benzodioxin-2-carboxylate

HRID 2393512Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2393512
[Cl-].[Cl-].[Cl-].[Al+3].[C:5](Cl)(=[O:7])[CH3:6].[O:9]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[O:12][CH:11]=[C:10]1[C:19]([O:21][CH2:22][CH3:23])=[O:20]>C(=S)=S>[C:5]([C:17]1[CH:16]=[CH:15][C:14]2[O:9][C:10]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:11][O:12][C:13]=2[CH:18]=1)(=[O:7])[CH3:6]

Komponenten

5

Edukt 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 10987416Ethyl 1,4-benzodioxin-2-carboxylate

Produkt 1

HCID 11806994Ethyl 6-acetyl-1,4-benzodioxin-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6348Carbon DisulfideLösungsmittel

Versuchsvorschrift

12.5 g of aluminum trichloride are added to a mixture of 4.27 g of acetyl chloride and 7.5 g of ethyl 1,4-benzodioxin-2-carboxylate in 150 ml of carbon disulfide at 0° C. The reaction mixture is stirred at room temperature for 14 hours. After acid hydrolysis with 50 ml of hydrochloric acid (2N) and extraction of the aqueous phase with dichloromethane, the organic phase is washed with saturated sodium hydrogen carbonate solution and then dried over magnesium sulfate. The acylated product is purified by chromatography on silica gel (eluent: petroleum ether/ethyl acetate, 7:3).

Aufarbeitung

  1. customAfter acid hydrolysis
  2. extractionwith 50 ml of hydrochloric acid (2N) and extraction of the aqueous phase with dichloromethane
  3. washthe organic phase is washed with saturated sodium hydrogen carbonate solution
  4. dry with materialdried over magnesium sulfate
  5. customThe acylated product is purified by chromatography on silica gel (eluent: petroleum ether/ethyl acetate, 7:3)

Quellen und Nachweise

ORD-Eintrag
ord-9301f14740614bc08d4370d2bbf5d2bb
Quelldatensatz
uspto-grants-1998_09
Patentnummer
US05807882

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