腈制备羧酸

产物官能团类型

1. NaOH法 2. HCl法

1. NaOH法

腈的碱性水解生成羧酸通常在高温(例如回流)下使用氢氧化物碱(例如 NaOH 或 KOH)和适当的溶剂(例如乙醇/水)进行。对碱敏感的底物可能不太耐受。


案例

To a solution of KOH (10 g, 178 mmol) in H2O (15 mL) and EtOH (15 mL) at RT was added the SM (3.92 g, 42 mmol) over 10 min. The reaction mixture was stirred at 90 C for 3.5 h, after which time it was concentrated in vacuo. The resulting residue was dissolved in H2O (10 mL) and acidified at 0 C with 6M HCl to pH 1. The mixture was extracted with DCM. The org layer was dried (MgSO4) and concentrated to provide the product as a colorless oil which was taken forward without further purification. [4.65 g, 98%]

Patent Reference: WO2015129926, page 108

2.HCl法

腈的酸性水解生成羧酸通常在高温(例如回流)下使用强酸(例如 HCl)进行。对酸敏感的底物可能不太耐受。


案例

The SM (600 mg, 1.68 mmol) in 10N HCl (20 mL) was stirred at 100 C for 5 h. The reaction mixture was cooled to RT and 5N LiOH was added to pH 6. The resulting precipitate was filtered and dried to provide the product which was used without further purification

Patent Reference: WO2007089768, page 230