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-chloromethylimidromenhaszole 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