Cycloheptanemethanol → Formylcycloheptane

To a stirred solution of cycloheptyl-methanol (1.28 g, 0.01 mol) in CH2Cl2 (50 ml) at room temperature was added portionwise PCC (3.23 g, 0.015 mol). The reaction turned almost instantly dark brown as was stirred at room temperature for 4 hours. The reaction was then diluted with Et2O (50 ml) and the solvent decanted away from the solid residue. The residue was washed with further Et2O (2×25 ml). The reaction mixture and combined washing were then filtered through a 10 g SiO2 chromatography cartridge and washed through with further Et2O (25 ml). The solvent was then removed under reduced pressure to yield the desired compound (1.08 g) as a colourless, pungent oil which was used without further purification.

1. customthe solvent decanted away from the solid residue
2. washThe residue was washed with further Et2O (2×25 ml)
3. washThe reaction mixture and combined washing
4. filtrationwere then filtered through a 10 g SiO2 chromatography cartridge
5. washwashed through with further Et2O (25 ml)
6. customThe solvent was then removed under reduced pressure

ORD record

ord-c7b24b45d7d44704b6aa8974fe4278bf

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08791303B2