Hydrochloric Acid → HCID 43395143, compound

Participants

Reaction Conditions

Reaction Steps

5.0 g (30 mmol) of 3-diethylaminophenol are dissolved in 80 ml dry toluene and cooled down to -78° C. Within 15 min 15 ml of a 2 molar LDA-solution are added. After warming up to room temperature this phenolate solution is added in dropwise to a solution of 2.7 ml (30 mmol) of methyl chloroacetate in 15 ml of dry toluene. The dark brown reaction mixture is stirred at room temperature for 3 hours, after then it is added to 300 ml of water. Then solution is made acidic by adding a little amount of 2 N HCl. Afterwards, the reaction mixture is extracted three times with 80 ml of chloroform each time. The organic phases are collected and are dried with MgSO4. After the drying agent is filtered off, the solvent has been stripped off on a rotary evaporator, a dark brown, highly viscous residue is obtained. Fractional distillation under the reduced atmosphere of an oil pump yields the analytically pure, slightly yellowish, viscous, liquid product, which quickly turns dark brown under the influence of light and air.

Provenance & Evidence