Water → HCID 57429402, compound

Participants

Reaction Steps

A solution of Dess Martin periodinane (4.1 g, 9.7 mmol, 1.1 eq) in dichloromethane (43 mL) was charged into a 250 mL three-necked round-bottom flask, equipped with a mechanical stirrer and a reflux condenser. 2-methyl-3-(3-methylcyclohexyl)propan-1-ol (1.5 g, 8.8 mmol) was added dropwise, followed by a mixture of water (127 L) in dichloromethane (127 mL) at ambient temperature, over 1 h. After stirring for 1 h at ambient temperature, the mixture was diluted with diethyl ether (100 mL) and washed with a 1:1 mixture of saturated aqueous NaHCO3 and 10% aqueous Na2S2O3 (50 mL) and brine (50 mL), dried over magnesium sulphate and concentrated. The crude product was chromatographed on a silica gel column with 5% EtOAc in hexane as elution agent giving 2-methyl-3-(3-methylcyclohexyl)propanal (800 mg, gc purity>90%; yield 54%).

Provenance & Evidence