1、腈的酸水解示例
A mixture of water (1150mL), commercial sulfuric acid (840 mL) and benzyl cyanide (700 g, 6 mol) was heated under a reflux condenser and stirred for three hours, cooled slightly, and then poured into 2 L of cold water. The mixture should be stirred so that a solid cake was not formed; the phenylacetic acid was then filtered off. The crude material was melted under water and washed by decantation several times with hot water. These washings, on cooling, deposited a small amount of phenylacetic acid which was filtered off and added to the main portion of material. The last of the hot water was poured off from the material while it was still molten, and it was then transferred to a Claisen distilling flask and distilled under reduced pressure. A small amount of water came over first and was rejected; about 20 mL, containing an appreciable amount of benzyl cyanide, then distils. This fraction was used in the next run. The distillate boiling at 176–189°/50 mmHg was collected separately and solidified on standing to give the product (630 g, 77.5%) which melts at 76~76.5°C.
Reference: Organic Syntheses Coll. Vol. 1, 436。
2、腈的碱水解示例
A mixture of 2-phenylpropanenitrile (13.2 g, 0.1 mol) and an aqueous solution of sodium hydroxide (10%, 60 mL) was heated with magnetic stirring in an oil bath at reflux temperature for 4.5 hr. The course of the reaction was monitored by gas-chromatographic analysis. After the solution was cooled to room temperature, it was extracted with diethyl ether to remove nonacidic material (primarily traces of amide). An aqueous solution of hydrochloric acid (15%, 50 mL) was added portionwise. The suspension that formed was poured into a separatory funnel and extracted with diethyl ether (3 × 50 mL). The combined organic extracts were washed with water (60 mL) and dried over sodium sulfate (25 g). After filtration, the solvent was removed by rotary evaporation, and the yellow liquid residue was
distilled under reduced pressure to afford 2-phenylpropionic acid (14.3 g, 93%) as a pale-yellow liquid.
Reference: Organic Syntheses Coll. Vol. 10, 640
3 、亚硝酸钠促进的腈的酸水解示例
A mixture of compound 1 (6.6 g, 35 mmol), conc. H2SO4 (29 ml), AcOH ( 58 ml) and water (115 ml) was heated at 120°C for 1h, then a solution of NaNO2 (4.0 g), in water (30 ml) was added at 90~100°C. After the mixture had been heated for 1 h, NaCl (40 g) was added to the hot mixture and the whole was cooled in an ice-bath. The precipitate was collected to give the crude free acid (6.2 g, 62%).
Reference: Chem. Pharm. Bull.; EN; 33; 8; 1985; 3336-3348.
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腈在硫酸/乙醇中加热回流可以直接得到相应的酯。
