Reacción #5716

Ecuación de reacción

toluene

benzoic anhydride

perchloric acid

→

rac-(2RS,3RS,5SR)-3-benzoyloxy-2-hexyl-5-undecyl-δ-valerolactone

Rendimiento 103.4%

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGwas stirred for 10 minutes
2. 2
   workup.STIRRINGThe mixture was stirred for a further 2.5 hours
3. 3
   ExtracciónThe reaction solution was extracted in toluene with 1N sodium hydroxide solution
4. 4
   SecadoThe combined toluene phases were dried
5. 5
   Filtraciónthe drying agent was filtered off under suction
6. 6
   Lavadowashed with toluene
7. 7
   OtroEvaporation of the solvent

Procedimiento

177.3 g of the δ-lactone from c) were suspended in 1250 ml of toluene while stirring. After the addition of 138.6 g of benzoic anhydride the mixture was stirred for 10 minutes. Then, 2.5 ml of perchloric acid were added. The mixture was stirred for a further 2.5 hours. The reaction solution was extracted in toluene with 1N sodium hydroxide solution and then with water. The combined toluene phases were dried, the drying agent was filtered off under suction and washed with toluene. Evaporation of the solvent gave 237.2 g (103.4%) of rac-(2RS,3RS,5SR)-3-benzoyloxy-2-hexyl-5-undecyl-δ-valerolactone, which was used in the next step without purification.

Fuente