Sodium Hydroxide → HCID 178520905, compound

Participants

Reaction Steps

Sodium hydroxide (0.25 mole) dissolved in minium water was treated with cyclohexylmercaptan (0.25 mole) and 700 ml dioxan. Chloropropionylferrocene (0.25 mole) was then added and the resulting mixture stirred on a steam bath for 3 hours. The mixture was diluted with water and extracted with chloroform. The organic liquors were washed successively with aqueous sodium hydroxide and water, dried and concentrated affording crude product. This was chromatographed through a silica gel column (20:1 ratio of silica to substrate) using initially 1% ethyl acetate/petroleum ether (60°-80°) then 3% ethyl acetate/petroleum ether as eluent. This afforded an oil which crystallised on cooling and trituration with petroleum ether. The solid was filtered off and washed with petroleum ether affording 3-(cyclohexylthio)propionyl ferrocene, mp 46.5°-48.5°, in 20% yield. Concentration of the petroleum ether liquors afforded a further 3% yield of product.

Provenance & Evidence