Preparation and application of (1-methyl-1H-imidazol-4-yl)methanol_Industrial additives

Background and overview^[1]

(1-Methyl-1H-imidazol-4-yl)methanol is an organic intermediate that can be obtained by reduction of 1-methyl-imidazole-4-carboxylic acid, and can be further chlorinated to prepare 1-methyl- 4-Chloromethylimiromenhaszole hydrochloride.

Preparation^[1]

To a suspension of 1-methyl-imidazole-4-carboxylic acid (11.4g, 90mmol) in THF (500ml) was added dropwise lithium aluminum hydride (1M solution in THF, 117ml) at 0°C. , 117 mmol), and the mixture was stirred at room temperature overnight and then at 50°C for 1 hour. Water (3 ml) was then added, Na_{rubber plasticizer 2}SO₄ was added, and the resulting precipitate was filtered on a diatomaceous earth pad. The filtrate was concentrated under reduced pressure to obtain the title compound (1-methyl-1H-imidazol-4-yl)methanol as a solid (8g, 78.95%), yield (8g, 78.95%), ¹ H NMR (300MHz, CDCl₃, ppm) δ: 7.25 (s, 1H), 6.7 (s, 1H), 5.25 (m, 1H), 4.4 (s, 2H), 3.45 (s , 3H).

Apply^[1]

(1-Methyl-1H-imidazol-4-yl)methanol can be used to prepare the intermediate 1-methyl-4-chloromethylimidazole hydrochloride. Here’s how:

To (1-methyl-1H-imidazol-4-yl)methanol (5g, 44.64mmol), CH₂Cl₂ ( Thionyl chloride (50 ml) was added dropwise to the solution, and the mixture was stirred at room temperature overnight, then at reflux for 3 hours, and then at room temperature for 1 hour. Then concentrate under reduced pressure. The residue was treated with ethylene oxide and the resulting precipitate was filtered and dried. 1-Methyl-4-chloromethylimidazole hydrochloride was obtained as a brown solid (4g, 53.81%), ¹H NMR (300MHz, d6-DMSO, ppm) δ: 9.25 (s , 1H), 7.8 (s, 1H), 4.95 (s, 2H), 3.9 (s, 3H).

References

[1] From PCT Int. Appl., 2004013134, 12 Feb 2004