Toluene → HCID 19090311, compound

Participants

Reaction Steps

Tetraethyl 1-(vinylphenyl)propane-2,2-bisphosphonate (4) was prepared from compound (3) and vinylbenzyl chloride, of which 70% was in meta- and 30% in para-form, in the following manner. In a flame dried two-necked flask equipped with a dropping funnel and protected with nitrogen gas 100 ml of dry toluene and 2.69 g (0.112 moles) of dry sodium hydride were introduced. Mixing was started and 30.0 g (0.099 moles) of compound (3) was dropped to the mixture. When the addition was complete and the release of hydrogen had ceased, stirring was continued for an additional hour at room temperature. Thereafter 18.3 g (0.12 moles) of vinylbenzyl chloride was dropped to the mixture, and stirring was continued under the protective gas at room temperature until the reaction was complete. This lasted from one to two weeks. The reaction mixture was concentrated on a rotary vacuum evaporator. The residue was dissolved in diethyl ether, washed three times with water, dried over sodium sulphate and the solvent evaporated in vacuum. 33.5 g (81 %) of the raw product (4) was obtained, of which about 80 % was compound (4) and 20% vinylbenzyl chloride. The raw product was used unpurified in the subsequent reaction.

Provenance & Evidence