3,4-Dimethoxytoluene → 1,2-Dimethoxy-4-methyl-5-(2-cyano-3-methoxy-2-propenyl)benzene

HRID 258558

Reaktionsgleichung

Reaktionsgleichung von HRID 258558
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH3:11])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH3:12][O:13][CH:14](OC)[C:15](=[CH2:18])[C:16]#[N:17]>C(Cl)Cl>[CH3:10][O:9][C:8]1[CH:7]=[C:6]([CH2:18][C:15]([C:16]#[N:17])=[CH:14][O:13][CH3:12])[C:5]([CH3:11])=[CH:4][C:3]=1[O:2][CH3:1]

Komponenten

4

Edukt 2

HCID 681263,4-DimethoxytolueneHCID 124234392-Dimethoxymethylacrylonitrile

Produkt 1

HCID 544881951,2-Dimethoxy-4-methyl-5-(2-cyano-3-methoxy-2-propenyl)benzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 10 g. of 3,4-dimethoxytoluene and 9.6 g. of 2-dimethoxymethylacrylonitrile in 200 ml. of dry methylene chloride was added dropwise at 0°, 2.3 ml. (0.0197 mole) of stannic chloride. The reaction mixture was stirred for 6 hours at 20°-25°, diluted with 500 ml. of ether, and the resulting solution washed with a 5% sodium bicarbonate solution until the aqueous layer remained basic. The combined aqueous washings were backwashed with ether and the organic layers were then combined and dried (MgSO4). The solvent was then removed under reduced pressure leaving an off-white residue of crude 1,2-dimethoxy-4-methyl-5-(2-cyano-3-methoxy-2-propenyl)benzene.

Aufarbeitung

  1. additiondiluted with 500 ml
  2. washof ether, and the resulting solution washed with a 5% sodium bicarbonate solution until the aqueous layer
  3. dry with materialdried (MgSO4)
  4. customThe solvent was then removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3a020de4b21c4801ae1838bb064b8492
Quelldatensatz
uspto-grants-1977_07
Patentnummer
US04033962

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