酯水解成羧酸

产物官能团类型

酯的水解条件

反应机理

  1. MeOH+H2O+MeOH
    2. 其他类型的碱也可使用，例如氢氧化钠、氢氧化钾、氢氧化锂。在某些反应中，也可以使用乙醇代替甲醇。
  2. MeOH+H2O+THF
    3. 其他类型的碱也可使用，例如氢氧化钠、氢氧化钾、氢氧化锂。1，4-二氧六环有时候也可以用来代替THF。根据所 使用的溶剂量的差异、温度和离子浓度的差异，有时候反应可能是两相的。
  3. MeOH+H2O+MeOH+THF
    4. 其他类型的碱也可使用，例如氢氧化钠、氢氧化钾、氢氧化锂。有时候可以用乙醇代替甲醇，1，4-二氧六环代替 THF,反应可能会形成两相。
  4. HCl(酸性条件)
    5. 酸性条件的水解是一个可逆的过程，因此需要大量的水参与驱使反应向酸的方向移动，形成羧酸。Fisher酯化反应 是该反应的逆反应。

案例1.碱性水解

To a solution of the SM (2.31 g, 7.77 mmol) in MeOH (50 mL) and H2O (2.8 mL) was added NaOH (0.46 g, 11.7 mmol). The mixture was heated to reflux for 16 h, then cooled and concentrated in vacuo. The crude was diluted with H2O (100 mL) and acidified with an aq solution of 2M HCl. This aq mixture was extracted with EtOAc (2 x 200 mL) and the combined org extracts were washed with brine (400 mL), dried (MgSO4), and concentrated in vacuo to provide to product as a yellow solid.

Patent Reference: WO2010032200, page 135

案例2.酸性水解

A solution of the SM (15.23 g, 37.06 mmol) in conc. HCl (21.80 mL), H2O (68.6 mL), and dioxane (192.6 mL) was stirred at reflux for 5 h. The mixture was concentrated to half its volume (~130 mL), neutralized with sat aq NaHCO3 to PH = 8-9, and extracted with EtOAc (3 x 80 mL). The combined organics were back-extracted with H2O (80 mL). The combined aq layers were acidified to pH = 3 with conc. HCl and extracted with EtOAc (3 x 80 mL). The combined organics were dried (Na2SO4) and concentrated to provide the product as a brown oil. [7.00 g, 48%]

Patent Reference: WO2015089337, page 206

反应机理

碱性水解