Dichloromethane → HCID 57429412, compound

Participants

Reaction Steps

2-[2-(3-isopropylcyclohexyl)propyl]-1,3-dioxolane (5 g, 20.8 mmol) and a 4:1 mixture of dichloromethane:acetone (300 mL) were charged into a 3 L three-necked round-bottom flask equipped with a reflux condenser and a mechanical stirrer. Iron (III) chloride hexahydrate (19.7 g, 72.8 mmol, 3.5 eq) was added at ambient temperature. The reaction mixture was then stirred at ambient temperature for 4 h and subsequently quenched at 5-10° C. with the addition of saturated aqueous NaHCO3 (500 mL). The organic phase was then washed with brine (500 mL), dried over magnesium sulphate and concentrated. The resulting crude product was distilled via a Vigreux column (1.3 mBar, 89° C.), to give 3-(3-isopropylcyclohexyl)butanal (23.9 g, gc purity>91%; yield 62%).

Provenance & Evidence