Reacción #89612

Ecuación de reacción

1,2,4-Trimethyl-bicyclo[2.2.1]heptane-2-carboxylic acid

methylene chloride

thionyl chloride

→

1,2,4-trimethyl-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester

Rendimiento 45.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.DISTILLATIONexcessive thionyl chloride was distilled out and methanol (100 mL)
2. 2
   workup.ADDITIONwas added
3. 3
   workup.ADDITIONpoured into saturated aqueous sodium bicarbonate
4. 4
   ExtracciónThe resulting mixture was extracted with toluene
5. 5
   workup.DISTILLATIONthe organic phase was distilled

Procedimiento

1,2,4-Trimethyl-bicyclo[2.2.1]heptane-2-carboxylic acid (obtained as detailed above) was dissolved in methylene chloride (50 mL), and added dropwise to thionyl chloride (100 mL) at 50° C. After 1 hour, excessive thionyl chloride was distilled out and methanol (100 mL) was added. The reaction mixture was stirred overnight and then poured into saturated aqueous sodium bicarbonate. The resulting mixture was extracted with toluene and the organic phase was distilled to provide 1,2,4-trimethyl-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester (65 g, 45% yield).

Fuente