Toluene → 4-Vinylcyclohexane-carbaldehyde

Participants

Reaction Steps

Next, 15 ml of solution of 5.4 g of the crude 4-vinyl-1-hydroxymethylcyclohexane in dichloromethane was added dropwise to a mixture of 9.1 g (42.1 mmol) of pyridinium chlorochromate and 50 ml of dichloromethane while being cooled with ice and stirred for 12 hours. The reaction mixture was filtered, the solvent was distilled off under a reduced pressure, and the residue thus obtained was subjected to silica gel column chromatography (eluent: toluene) to obtain 2.1 g of a crude 4-vinylcyclohexane-carbaldehyde. As the result of analysis of this product by gas chromatography, it was found out to be a mixture of cis/trans=31/69.

Provenance & Evidence