Toluene → 1-Dodecyl-4-ethenylbenzene

Participants

Reaction Steps

A 2 l round-bottom flask which had been provided with a water separator and a reflux condenser was charged initially with 1.2 liters of toluene and then with (p-dodecylphenyl)methylcarbinol (50.082 g=0.173 mol) and p-toluenesulphonic acid monohydrate (0.679 g=3.6 mmol). The mixture was heated to reflux with constant stirring and kept at boiling until no further water separated out. Once the reaction mixture had been cooled to room temperature, the organic phase was extracted by shaking twice with 500 ml each time of water and once with 250 ml of saturated sodium chloride solution. After drying over magnesium sulphate, the solvent was drawn off on a rotary evaporator. A yellow oil was obtained. Subsequently, the two batches were combined. The crude product was purified by column chromatography on 400 g of silica gel 60 with hexane as the eluent, and a fraction size of 100 ml was selected.

Provenance & Evidence