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

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Reaction Steps

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).

Provenance & Evidence