Formaldehyde → Methyl 4-[[2-ethyl-4-methyl-1H-imidazol-1-yl]methyl]benzoate

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Reaction Steps

Methyl 4-[[2-ethyl-4-methyl-1H-imidazol-1-yl]methyl]benzoate compound was prepared from 2-ethyl-4-methyl-imidazole and (4-carbmethoxy)benzylbromide in an analogous fashion as described in Example 11. A solution of the above imidazole (2.17 g, 8.14 mmol), NaOAc 1.17 g), 37% HCHO (10 mL), and AcOH (1.2 mL) was heated under reflux for 22 hours. The solution was evaporated under vacuo, and the residue was stirred with 10 mL of 20% NaOH solution for 2 hours. It was diluted with water and the solution was extracted with CH2Cl2. The extract was washed with water, dried, and evaporated to an oil. It was chromatographed (CH2Cl2 /MeOH, 2-5%) to give 1.0 g of the desired hydroxymethyl compound as a foam. MS (CI) 288 (m).

Provenance & Evidence