Dichloromethane → 2-Methoxy-5-methylbenzaldehyde

HRID 544328

Reaktionsgleichung

Reaktionsgleichung von HRID 544328
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.C(Cl)Cl.[CH3:13][O:14]C(Cl)Cl>[Ti](Cl)(Cl)(Cl)Cl.O>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][C:4]=1[CH:13]=[O:14]

Komponenten

6

Edukt 3

HCID 6344DichloromethaneHCID 77314-MethylanisoleHCID 21004Methane, dichloromethoxy-

Produkt 1

HCID 5913982-Methoxy-5-methylbenzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24193Titanium TetrachlorideKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

4-Methylanisole (12.2 g., 0.1 mole) in 300 ml. of methylene chloride was cooled to 0° C. Titanium tetrachloride (3.8 g., 0.2 mole) was added followed by the dropwise addition of 1,1-dichloromethyl methyl ether (13.8 g., 0.12 mole) over 3 minutes. After stirring for 30 minutes at 0° C., the reaction mixture was poured into 600 ml. of water. The aqueous phase was extracted with two further portions of methylene chloride. The combined organic phase/extracts was washed with brine, dried over anhydrous magnesium sulfate and evaporated to yield 2-methoxy-5-methylbenzaldehyde as an oil [15 g., 100%; ir (CH2Cl2) 1678, 1608, 1488 cm-1 ].

Aufarbeitung

  1. additionthe reaction mixture was poured into 600 ml
  2. extractionThe aqueous phase was extracted with two further portions of methylene chloride
  3. washThe combined organic phase/extracts was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-c7b59fdffbaf496d9fcccd2a12d8ab79
Quelldatensatz
uspto-grants-1984_05
Patentnummer
US04448971

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