Reacción #484426

Ecuación de reacción

NaHCO3

(rac)-3-mercapto-3-methyl-hexan-1-ol

3,5-dinitrobenzoyl chloride

→

(rac)-3,5-dinitro-benzoic acid 3-mercapto-3-methyl-hexyl ester

Rendimiento 84.2%

Disolventes

CCl4

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe organic layer was separated
2. 2
   Lavadowashed with 15 ml of brine
3. 3
   Secadodried over MgSO4
4. 4
   Concentraciónconcentrated in vacuo
5. 5
   OtroThe residue was purified by flash-chromatography (silicagel, hexane/EtOAc 4:1)

Procedimiento

To a solution of 5.0 g (34 mmol) of (rac)-3-mercapto-3-methyl-hexan-1-ol in 20 ml of CCl4 was added in portions 8.6 g (37 mmol) of 3,5-dinitrobenzoyl chloride. The mixture was stirred for 72 h, then 10 ml of a saturated NaHCO3 solution was added, the organic layer was separated, washed with 15 ml of brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash-chromatography (silicagel, hexane/EtOAc 4:1) and gave 9.8 g (84%) of (rac)-3,5-dinitro-benzoic acid 3-mercapto-3-methyl-hexyl ester.

Fuente