Sulfuric Acid → Bicyclohexyl-3-ene

Participants

Reaction Steps

A 1 L four-necked flask equipped with a mechanical stirrer, a thermometer, and a Dean-Stark water separator was charged with 4-cyclohexyl-1-cyclohexanol (0.549 mol), sulfuric acid (0.055 mol), sodium sulfate (0.055 mol), distilled water (40 g), and xylene (100 g), and they were heated and refluxed for 3 hours. After completion of the reaction, the reaction mixture was filtered with a glass filter, the solvent was removed by vacuum distillation, and purification was carried out by silica gel column chromatography (silica gel 60 (70-230 mesh), manufactured by Merck Ltd., elution solvent: n-hexane). The reaction product thus obtained was subjected to vacuum distillation using a kugelrohr distillation apparatus at 120° C./666 Pa to give 81.04 g (90% yield) of 4-cyclohexyl-1-cyclohexene (Formula (18) below). The results of 1H-NMR of this product are shown below.

Provenance & Evidence