腈的醇解催化酯

在酸催化下，氰基可以醇解如此一来生成衍生物。通常用于的催化剂是浓硝酸或氯化氢，只适用于伯醇，因为舅醚仲醇在硝酸关键作用持续性生成乙烯，硝酸和放出的氧成盐。

腈的醇解，醇兼作溶剂，其用量相当大，一般是理论量的4～5倍；硝酸的用量也要至少理论用量的0.5～1倍。

1-(4-Cyanophenyl)-piperazine (11 mmol) was dissolved in 5 N a solutionof concentrated sulfonic acid and methanol (15 ml) and stirred in a sealed tubeat 110 ℃for 3 h. After evaporationof the solvent, the residue was dissolved in water and extracted with ethylacetate. Addition of sodium carbonate to the water phase until pH 9 results inthe precipitation of a white solid which was filtered off and dried (vacuum). Awhite powder with R f 0.59 (CH 2 Cl 2 /MeOH = 9:1)was obtained. 4-piperazin-1-yl-benzoic acid methyl ester。

1-[2,2-Bis(4-cyanobenzylthio)ethyl]-1H-imidazole hydrochloride (1.43 g)was added to methanol (50 mL) which had been saturated with hydrogen chlorideat 0 ℃. The resulting solutionwas stirred under reflux for 20 h and then concentrated. The gummy residue was partitioned between CH 2 Cl 2 and aqueous NaHCO 3 , and the CH 2 Cl 2 layer waswashed with brine and dried over Na 2 SO 4 . Removal of the CH 2 Cl 2 left a gum which was hromatographed on silicic acid (60 g) with CH 2 Cl 2 /CH 3 OH (95:5), to afford 1.1 g of the free base of the titlecompound as a viscous oil. Treatment of a solution of the base in CH 3 OH-etherwith hydrogen chloride provided colorless crystals of 1-[2,2-Bis(4-carbomethoxybenzylthio)ethyl]-1H-imidazoleHydrochloride.