反应 #66728

反应方程式

formic acid

sulfuric acid

5-hydroxy-2-adamantanone

formic acid

methanol

→

desired product

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

反应条件

后处理

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

实验过程

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+).

来源