Reacción #78907

Ecuación de reacción

4-(diethoxyphosphoryl)-benzoic acid ethyl ester

4-(Diethoxyphosphoryl)-benzoic Acid Ethyl Ester

lithium hydroxide

→

4-(Diethoxyphosphoryl)-benzoic Acid

Disolventes

water

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe resulting reaction mixture
2. 2
   ConcentraciónThe reaction mixture was concentrated
3. 3
   Otroto remove methanol
4. 4
   workup.ADDITIONdiluted with brine
5. 5
   Extracciónextracted with EtOAc (3×100 mL) until the aqueous layer
6. 6
   SecadoThe combined organics were dried over Na2SO4
7. 7
   Concentraciónconcentrated on a rotary evaporator
8. 8
   OtroThe desired product was purified by crystallization from hexane/ethyl acetate (2.37 g), m.p. 101° C

Procedimiento

To a solution of 4-(diethoxyphosphoryl)-benzoic acid ethyl ester (2b) (2.46 g, 8.59 mmol) in methanol (86 mL) was slowly added lithium hydroxide (monohydrate, 0.36 g, 8.59 mmol) in water (86 mL). The resulting reaction mixture was stirred at room temperature for 4 hours. The reaction mixture was concentrated to remove methanol and diluted with brine, then extracted with EtOAc (3×100 mL) until the aqueous layer showed little or no evidence of product by HPLC. The combined organics were dried over Na2SO4 and concentrated on a rotary evaporator. The desired product was purified by crystallization from hexane/ethyl acetate (2.37 g), m.p. 101° C. 1H NMR (300 MHz, CDCl3) δ (ppm)): 1.27 (t, J=7.03 Hz, 6H), 4.03 (q, J=7.03 Hz, 4H), 7.85 (m, 2H), 8.09 (m, 2H), 12.65 (bs, 1H). 31P NMR (121 MHz, CDCl3) δ21.611.

Fuente