Reacción #364762

Ecuación de reacción

Neopentyl alcohol

2-methyl-5-nitro-benzenesulfonyl chloride

pyridine

dioxane

→

title compound

Rendimiento 57.2%

2-Methyl-5-nitro-benzenesulfonic Acid, 2.2-Dimethylpropyl Ester

Rendimiento 57.2%

Disolventes

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroA water cooled condenser was attached
2. 2
   Temperaturathe material was heated to reflux
3. 3
   LavadoThe organic layer was washed with water
4. 4
   SecadoAfter drying with MgSO4 the solution
5. 5
   Concentraciónwas concentrated

Procedimiento

Neopentyl alcohol (0.75 g, 8.50 mmol) was added to a solution of commercially available 2-methyl-5-nitro-benzenesulfonyl chloride (1.00 g, 4.20 mmol), pyridine (1.72 mL, 21.2 mmol and anhydrous dioxane (40 mL). A water cooled condenser was attached and the material was heated to reflux. After stirring for two days the mixture was cooled to room temperature and diluted with ethyl acetate (350 mL). The organic layer was washed with water, then 1 N HCl solution, and finally brine. After drying with MgSO4 the solution was concentrated to afford 690 mg of the title compound as a yellow solid.(55%): 1HNMR (DMSO-6) δ8.57 (d, J=2 Hz, 1H), 8.51 (dd, J=8 Hz, 2 Hz, 1H), 7.85 (d, J=8 Hz, 1H), 3.78 (s, 2H), 2.70 (s, 3H), 0.88 (s, 9H); MS (EI): [M+] 287; Anal. Calc. for C12H17NO5S: C, 50.16; H, 5.96; N, 4.88. Found: C, 49.83; H, 5.69; N, 4.90.

Fuente