Water → 1,11-Bis(4-nitrophenoxy)undecane

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Reaction Steps

A 4-necked flask, equipped with a mechanical stirring device, a dropping funnel, a reflux condenser and a thermometer, is charged with 8.9 g (65 mmol) of paranitrophenol in 20 ml of dimethylsulphoxide. To this solution there are added 2.56 g (64 mmol) of solid pelletized sodium hydroxide. The resultant mixture is heated to 100° C. on an oil bath, until a homogeneous solution is obtained. To the latter solution there are cautiously added 10 g (32 mmol) of 1,11-dibromoundecane, dissolved in 20 ml of dimethylsulphoxide, and, on completion of this addition, the reaction mixture is held at 100° C. for 2 hours. Finally, the reaction mixture is cooled and poured into one litre of continually stirred water, the result being the formation of a solid precipitate which is collected on a filter and repeatedly washed with water. The washed solid is crystallized from ethyl alcohol and 8.8 g of 1,11-bis(4-nitrophenoxy)undecane is obtained (yield 64%).

Provenance & Evidence