Sodium Carbonate → HCID 15354815, compound

Participants

Reaction Conditions

Reaction Steps

In a 1 L three-necked round-bottom flask equipped with a mechanical stirrer and a reflux condenser were introduced DMF (300 mL), 3-bromo toluene (66.3 g, 0.39 mol), of crotyl alcohol (99 mL, 1.16 mol, 3 eq), sodium carbonate (102.5 g, 0.97 mol, 2.5 eq), tetrabutyl-ammonium bromide (107.6 g, 0.39 mol, 1 eq), palladium acetate (7.8 g, 11.6 mmol, 3 mol %) and tri-o-tolyl phosphine (11.8 g, 38.7 mmol, 0.1 eq). After stirring for 1 h at 100-105° C., the reaction mixture was cooled to ambient temperature. The reaction mixture was filtered over celite. The organic phase thus obtained was diluted with MTBE (800 mL) and washed three times with water (500 mL portions), dried over magnesium sulphate and concentrated. The resulting crude product was fractionally distilled with a Vigreux column (1 mBar, 70-81° C.) to give a colourless oil (39.6 g, gc purity 90%). The oil was chromatographed on a silica gel column with 7% EtOAc in hexane as elution agent giving 3-(3-methylphenyl)butanal (12.5 g, gc purity>99%; yield 36%).

Provenance & Evidence