Reacción #66728

Ecuación de reacción

formic acid

sulfuric acid

5-hydroxy-2-adamantanone

formic acid

methanol

→

desired product

4-Oxo-adamantane-1-carboxylic acid methyl ester

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwere added dropwise over the course of 2 h
2. 2
   workup.STIRRINGstirred at room temperature for 2 h
3. 3
   ExtracciónThe aqueous layer was extracted with dichloromethane three times
4. 4
   Secadothe combined organic layer was dried over sodium sulphate
5. 5
   Otroevaporated to dryness

Procedimiento

38 mL of fuming sulfuric acid were placed in a two necked flask and warmed to 60° C. 1.5 g of 5-hydroxy-2-adamantanone, dissolved in formic acid (8.5 ml) were added dropwise over the course of 2 h. Another 9 mL of formic acid were added over a period of 2 h and stirring was continued at 60° C. for 1 h and at room temperature overnight. Under ice cooling, the reaction mixture was poured on 100 mL of dry methanol, stirred at room temperature for 2 h and subsequently poured onto 400 mL of ice. The aqueous layer was extracted with dichloromethane three times, the combined organic layer was dried over sodium sulphate and evaporated to dryness to give 1.64 g of the desired product. Rt=1.75 min (5). Detected mass: 209.2 (M+H+).

Fuente