Dichloromethane → Ethyl 4,5-dichloro-6-formyl-1,3-benzodioxole-2-carboxylate

HRID 1089172Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1089172
[Cl:1][C:2]1[C:10]2[O:9][CH:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[O:7][C:6]=2[CH:5]=[CH:4][C:3]=1[Cl:16].Cl[CH:18](Cl)[O:19]C.C(Cl)Cl>[Ti](Cl)(Cl)(Cl)Cl.C(OCC)(=O)C>[Cl:1][C:2]1[C:10]2[O:9][CH:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[O:7][C:6]=2[CH:5]=[C:4]([CH:18]=[O:19])[C:3]=1[Cl:16]

Komponenten

6

Edukt 3

HCID 6344DichloromethaneHCID 21004Methane, dichloromethoxy-2×HCID 14748637Ethyl 4,5-dichloro-1,3-benzodioxole-2-carboxylate

Produkt 1

HCID 14748638Ethyl 4,5-dichloro-6-formyl-1,3-benzodioxole-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24193Titanium TetrachlorideKatalysator2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

3.52 ml of titanium tetrachloride are added dropwise to a mixture of 4.0 g of ethyl 4,5-dichloro-1,3-benzodioxole-2-carboxylate, 2.12 ml of dichloromethoxymethane and 60 ml of methylene chloride at -60° C. and the mixture is stirred at room temperature for 2 days. 2.1 ml of dichloromethoxymethane and 2.1 ml of titanium tetrachloride are added to the reaction mixture at -60° C. and the mixture is stirred at room temperature for 18 hours. The reaction mixture is poured into a mixture of ethyl acetate and an aqueous sodium bicarbonate solution, and the organic layer is separated. The organic layer is washed with water, dried and evaporated to remove solvent. The residue is purified by silica gel column chromatography to give 3.21 g of ethyl 4,5-dichloro-6-formyl-1,3-benzodioxole-2-carboxylate.

Aufarbeitung

  1. stirringthe mixture is stirred at room temperature for 18 hours
  2. customan aqueous sodium bicarbonate solution, and the organic layer is separated
  3. washThe organic layer is washed with water
  4. customdried
  5. customevaporated
  6. customto remove solvent
  7. customThe residue is purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3632f59cf89f46bf8e4434552b5e1fcd
Quelldatensatz
uspto-grants-1990_10
Patentnummer
US04965282

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