Methyl iodide → 3,5-DI-Tert-butyl-4-methoxybenzaldehyde

HRID 21615

Reaktionsgleichung

Reaktionsgleichung von HRID 21615
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[CH3:18]I.[CH3:20][O:21]C(Cl)Cl.[Sn](Cl)(Cl)(Cl)Cl>O.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(Cl)Cl.CCOCC>[C:11]([C:7]1[CH:8]=[C:9]([CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]=1[O:15][CH3:18])[CH:20]=[O:21])([CH3:14])([CH3:13])[CH3:12]

Komponenten

10

Edukt 5

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 21004Methane, dichloromethoxy-HCID 24287Tin tetrachlorideHCID 314052,6-Di-tert-butylphenol

Produkt 1

HCID 129109393,5-DI-Tert-butyl-4-methoxybenzaldehydeAusbeute 47,7 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 66133Benzyl triethylammonium chlorideKatalysatorHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture containing 2 g (9.7 mmol) 2,6-di-tert-butyl phenol, 0.4 g NaOH dissolved in 4 ml water, 13.7 g (60.1 mmol) benzyl triethyl ammonium chloride and 12 g (84.5 mmol) methyl iodide was heated at 45° for 18 h. After purification 0.67 g 2,6-di-tert-butyl anisol was obtained. This compound (1.46 g, 6.63 mmol) was formylated by reaction at 0° C. with dichloromethyl methyl ether (1.15 g, 10 mmol) in presence of tin tetrachloride (3.1 g, 11.9 mmol) in 20 ml CH2Cl2. After hydrolysis and extraction into ether, 1.15 g of 3,5-di-tert-butyl-4-methoxybenzaldehyde were obtained (MS: m/e=248: M+; 233=M+ --CH3).

Aufarbeitung

  1. customAfter purification 0.67 g 2,6-di-tert-butyl anisol
  2. customwas obtained

Quellen und Nachweise

ORD-Eintrag
ord-10bd30426ab0424eb72c822219e8e9e9
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05424303

Verknüpfte Notizen

Wird geladen…