tert-Butyl hydroperoxide → Ethyl 6-acetyl-2,3-dihydro-1,4-benzodioxine-2-carboxylate

HRID 1756026

Reaktionsgleichung

Reaktionsgleichung von HRID 1756026
[CH2:1]([C:3]1[CH:17]=[CH:16][C:6]2[O:7][CH:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:9][O:10][C:5]=2[CH:4]=1)[CH3:2].C([O:22]O)(C)(C)C>C(Cl)Cl.[O-2].[O-2].[O-2].[Cr+6]>[C:1]([C:3]1[CH:17]=[CH:16][C:6]2[O:7][CH:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:9][O:10][C:5]=2[CH:4]=1)(=[O:22])[CH3:2]

Komponenten

5

Edukt 2

HCID 6410tert-Butyl hydroperoxideHCID 15210220Ethyl 6-ethyl-2,3-dihydro-1,4-benzodioxin-2-carboxylate

Produkt 1

HCID 15210221Ethyl 6-acetyl-2,3-dihydro-1,4-benzodioxine-2-carboxylateAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 10219390chromium (VI) trioxideKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Add 2 g (8.5 mmol) of ethyl 6-ethyl-2,3-dihydro-1,4-benzodioxin-2-carboxylate dissolved in 5 cm3 of anhydrous methylene chloride to a mixture at 0° C. of 0.042 g (0.42 mmol) of chromium trioxide and 5.35 g (59.3 mmol) of 70% tert-butyl hydroperoxide in 30 cm3 of methylene chloride. Stir for 2 hours at 0° C. and then for 72 hours at room temperature. The crude product obtained by concentrating to dryness is purified by chromatography on a silica column (eluant: methylene chloride). Ethyl 6-acetyl-2,3-dihydro-1,4-benzodioxin-2-carboxylate is thereby obtained in a yield of 62%. Melting point: 60° C.

Aufarbeitung

  1. waitfor 72 hours at room temperature
  2. customThe crude product obtained
  3. concentrationby concentrating to dryness
  4. customis purified by chromatography on a silica column (eluant: methylene chloride)

Quellen und Nachweise

ORD-Eintrag
ord-d687941ae6164db7abd9fc2137968029
Quelldatensatz
uspto-grants-1995_08
Patentnummer
US05439909

Verknüpfte Notizen

Wird geladen…