Hydrochloric Acid → ((Prop-2-yn-1-yloxy)methyl)benzene

Participants

Reaction Conditions

Reaction Steps

4.6 g (192 mmol) of sodium hydride was charged in a 200 ml three-necked flask provided with a 100 ml dropping funnel with a bypass and vacuum-dried in nitrogen stream. Then, thereto was added 100 ml of tetrahydrofuran, followed by cooling to 0° C. Furthermore, 11.2 ml (192 mmol) of propargyl alcohol diluted with 100 ml of tetrahydrofuran was gradually added thereto. After stirring at this temperature for 30 minutes, 22.3 ml (160 mmol) of chloromethylbenzyl ether diluted with 20 ml of tetrahydrofuran was added dropwise, followed by stirring for 30 minutes. After further stirring for 1 hour at room temperature, the reaction was stopped by saturated aqueous ammonium chloride solution and the reaction mixture was rendered weakly acidic with 3N aqueous hydrochloric acid solution and extracted with methylene chloride. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by vacuum distillation and then the ether (1) was obtained by vacuum distillation. Boiling point: 80-83° C./ 0.5 mmHg, Yield: 90%

Provenance & Evidence