Water → 2,3,4,5-Tetramethoxy-6-methylbenzaldehyde

HRID 1527657Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1527657
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[C:6]([O:13][CH3:14])=[CH:5][C:4]=1[CH3:15].[CH3:16][O:17]C(Cl)Cl.O>C(Cl)Cl.CCOC(C)=O.Cl[Ti](Cl)(Cl)Cl>[CH3:15][C:4]1[C:5]([CH:16]=[O:17])=[C:6]([O:13][CH3:14])[C:7]([O:11][CH3:12])=[C:8]([O:9][CH3:10])[C:3]=1[O:2][CH3:1]

Komponenten

7

Edukt 3

HCID 962WaterHCID 21004Methane, dichloromethoxy-HCID 98777642,3,4,5-Tetramethoxytoluene

Produkt 1

HCID 148523342,3,4,5-Tetramethoxy-6-methylbenzaldehydeAusbeute 89,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24193Titanium TetrachlorideKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

According to the procedure by Ohkawa et al.,15 6 (0.690 g, 3.25 mmol) was dissolved in CH2Cl2 (2.0 mL) in a flame-dried 25 mL round bottom flask and cooled to 0° C. α,α-dichloromethyl methyl ether (0.85 ml, 9.6 mmol) was then added at 0° C., followed by TiCl4 (1 M in CH2Cl2, 9.0 ml, 9.0 mmol) at 0° C. The reaction was warmed slowly to room temperature and stirred for 6 hours under argon. The reaction was then poured into chilled water and stirred for 10 minutes. The reaction was diluted with EtOAc, washed with brine, dried over MgSO4, filtered, and condensed. The crude oil was then purified by flash chromatography (1:49 EtOAc:hexanes if made via p-cresol; 3:17 EtOAc:hexanes if made via Wolffe-Kishner reduction) to provide 7 (0.696 g, 2.90 mmol, 89%) as a yellow oil.

Aufarbeitung

  1. additionwas then added at 0° C.
  2. additionThe reaction was then poured
  3. stirringstirred for 10 minutes
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customcondensed
  8. customThe crude oil was then purified by flash chromatography (1:49 EtOAc:hexanes if made via p-cresol; 3:17 EtOAc:hexanes if made via Wolffe-Kishner reduction)

Quellen und Nachweise

ORD-Eintrag
ord-72548506d25d41eca5126bd34985cf4b
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09089605B2

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