Veratrole → 1-(Chloromethyl)-2,3-dimethoxybenzene

HRID 1589238Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1589238
COC1C=CC=CC=1[O:9][CH3:10].Br[CH2:12][O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]C.[Cl:22][Sn](Cl)(Cl)Cl.COC1C=C2C(CC3C(CC4C(C2)=CC(OC)=C(OC)C=4)=CC(OC)=C(OC)C=3)=CC=1OC>ClCCCl>[Cl:22][CH2:20][C:19]1[C:14]([O:13][CH3:12])=[C:15]([O:9][CH3:10])[CH:16]=[CH:17][CH:18]=1

Komponenten

6

Edukt 4

HCID 7043VeratroleHCID 24287Tin tetrachlorideHCID 273730CyclotriveratryleneHCID 4989778Bromomethyloctylether

Produkt 1

HCID 27583941-(Chloromethyl)-2,3-dimethoxybenzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

0.138 g (1 mmole) of 1,2-dimethoxybenzene (veratrol) were reacted with 0.223 g (1 mmole) of bromomethyl octylether in 5 ml 1,2-dichloroethane in the presence of 0.12 ml (1 mmole) SnCl4 at room temperature for 1 hour. After washing with HCl and water, followed by drying on Na2SO4 the product was isolated by the evaporation of the solvent. The product (0.275 g) corresponds by mp., NMR and analysis to cyclotriveratrylene (A. J. Lindsey. J. Chem. Soc. 1685 (1965) obtained by trimerization of 3-chloromethyl-1,2-dimethoxybenzene.

Aufarbeitung

  1. washAfter washing with HCl and water
  2. customby drying on Na2SO4 the product
  3. customwas isolated by the evaporation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-75b05863f7314d9eb3436433db188e9b
Quelldatensatz
uspto-grants-1986_02
Patentnummer
US04568700

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