Dichloromethane → HCID 57429412, compound

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%).

1. customequipped with a reflux condenser and a mechanical stirrer
2. customsubsequently quenched at 5-10° C. with the addition of saturated aqueous NaHCO3 (500 mL)
3. washThe organic phase was then washed with brine (500 mL)
4. dry with materialdried over magnesium sulphate
5. concentrationconcentrated
6. distillationThe resulting crude product was distilled via a Vigreux column (1.3 mBar, 89° C.)

ORD record

ord-72638a6366114565a1e5a9bfc759e8a1

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08709994B2