Dimethyl Sulfate → HCID 21516864, compound

Participants

Reaction Conditions

Reaction Steps

55.0 g (0.275 mole) of a 20% aqueous sodium hydroxide solution was added dropwise to a mixture of 90.0 g (0.5 mole) of tricyclo[5.2.1.02,6 ]decane-2-carboxylic acid (mixture of endo- and exo-compounds) and 69.3 g (0.55 mole) of dimethyl sulfate over one hour under stirring at 50° C. After completion of the addition, stirring was continued at that temperature for 30 minutes. After completion of the stirring, the mixture was allowed to stand at room temperature for a while to form layers. The lower aqueous layer was taken out. The temperature was elevated again to 50° C. 55.0 g (0.275 mole) of sodium hydroxide in a 20% aqueous solution was added dropwise to the remainder over one hour under stirring at 50° C. After completion of the addition, the mixture was stirred at that temperature for 30 minutes. Then, 16.5 g (0.0825 mole) of a 20% aqueous sodium hydroxide solution was added thereto and the whole mixture was stirred at 100° C. for 45 minutes in order to decompose unreacted dimethyl sulfate. The mixture was allowed to cool and divided into layers. After the distillation, 88.3 g (yield 91.0%) of pure methyl tricyclo[5.2.1.02,6 ]decane-2-carboxylate was obtained.

Provenance & Evidence