Methanol → HCID 178519906, compound

Participants

Reaction Conditions

Reaction Steps

5-[4-(2-Methyl-4-benzofuranyloxymethyl)phenyl]tetrazole (1.224 g, 0.004 M) was dissolved in a mixture of dry methanol (130 ml) and dry dimethylformamide (20 ml), and cooled to -65° C. with stirring and exclusion of moisture. Ozonised air was bubbled through the solution at a rate of 20 liters/hr for 1 hr. Nitrogen was then bubbled through the solution (5 mins). to remove excess ozone before the addition of dimethyl sulphide (1.2 ml). The mixture was allowed to warm to room temperature overnight (16 hr). The solvent was removed in vacuo and the residual oil dissolved in ethyl acetate and washed with 2 N hydrochloric acid, water, and extracted with sodium bicarbonate solution. The combined extracts were acidified with 2 N hydrochloric acid to give a solid which was filtered off and dried. This mixture of 5-[4-(2-formyl-3-hydroxyphenoxymethyl)phenyl]tetrazole and 5-[4-(3-acetoxy-2-formylphenoxymethyl)phenyl]tetrazole was suspended in 95% ethanol (20 ml) and 1N sodium hydroxide (20 ml) and stirred at room temperature (1 hr). The solution was evaporated and the residue diluted with water and acidified. The resulting solid was filtered off, washed with water, dried and recrystallised form ethanol/water to give 5-[4-(2-formyl-3-hydroxyphenoxymethyl)phenyl]tetrazole as the 0.5 hydrate, m.p. 206°-206.5° C. (Found: C, 59.00; H, 4.29; N, 18.46. C15H12N4O3 0.5H2O requires C, 59.01; H, 4.29; N, 18.35%).

Provenance & Evidence