Reacción #43561

Ecuación de reacción

4,4-Dimethyl-pentanoic acid methyl ester

NaOH

→

4,4-dimethyl-pentanoic acid

Rendimiento 85.0%

Disolventes

CH2Cl2

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónthe aqueous layer was extracted with CH2Cl2 (50 mL×3)
2. 2
   Extracciónextracted with ethyl acetate (50 mL×3)
3. 3
   SecadoThe combined ethyl acetate fractions were dried over MgSO4
4. 4
   Filtraciónfiltered
5. 5
   Otroevaporated

Procedimiento

4,4-Dimethyl-pentanoic acid methyl ester (7.0 g, 48.5 mmol, 1.0 eq.) was treated with a solution of NaOH (4.0 g, 100 mmol, 2.1 eq.) in water (5 mL). The homogeneous solution was allowed to stir for 4-5 hours. The reaction was diluted with CH2Cl2 and the aqueous layer was extracted with CH2Cl2 (50 mL×3). The aqueous layer was acidified with 6M HCl to pH˜1.5 and extracted with ethyl acetate (50 mL×3). The combined ethyl acetate fractions were dried over MgSO4, filtered and evaporated to provide 4,4-dimethyl-pentanoic acid (5.35 g, 41.1 mmol, 85%) as a colorless oil: 1H NMR (CDCl3, 400 MHz) δ 0.89 (s, 9H), 1.53-1.57 (m, 2H), 2.26-2.30 (m, 2H).

Fuente