Reacción #364635

Ecuación de reacción

sodium carbonate

4-trifluoromethylbenzoic acid

2,2-dimethyl-propyl alcohol

sulfuric acid

→

4-trifluoromethyl-benzoic acid, 2,2-dimethyl-propyl ester

Rendimiento 99.5%

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaat reflux for 4 hours
2. 2
   Otrothe layers were separated
3. 3
   LavadoThe organic layer was washed with saturated aqueous sodium carbonate (250 mL), and brine (100 mL)
4. 4
   Concentraciónwas concentrated

Procedimiento

To a suspension of 4-trifluoromethylbenzoic acid (75.0 g, 394 mmol) and 2,2-dimethyl-propyl alcohol (70.5 g, 800 mmol) in toluene (500 mL) was added concentrated sulfuric acid (3.0 mL). The mixture was stirred at reflux for 4 hours, cooled to room temperature, poured into saturated aqueous sodium carbonate (250 mL) and the layers were separated. The organic layer was washed with saturated aqueous sodium carbonate (250 mL), and brine (100 mL), and was concentrated to give 4-trifluoromethyl-benzoic acid, 2,2-dimethyl-propyl ester (102 g, 99% yield) as a yellow liquid: Rf: 0.66 (ethyl acetate/hexanes 25/75); IR 2932, 1727, 1327, 1280, 1133, 1066, 862, 775, 704 cm−1; 1H NMR (400 MHz, CDCl3) δ8.16 (d, J=7.9 Hz, 2H), 7.70 (d, J=8.1 Hz, 2H), 4.04 (s, 2H), 1.04 (s, 9); 13C NMR (100 MHz, CDCl3) δ26.51, 31.61, 74.72, 123.63 (q, J=272.7 HZ), 125.4, 129.9, 133.7, 134.35 (q, J=31.7 Hz), 165.35.

Fuente