Sodium Carbonate → HCID 57429418, 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 (200 mL), 1-bromo-3-tert-butylbenzene (54.3 g, 0.25 mol), crotyl alcohol (65 mL, 0.76 mol, 3 eq), sodium carbonate (66.2 g, 0.62 mol, 2.5 eq), tetrabutyl ammonium bromide (69.5 g, 0.25 mol, 1 eq), palladium acetate (5.05 g, 7.5 mmol, 3 mol %) and tri-o-tolyl phosphine (7.6 g, 25 mmol, 0.1 eq). After stirring for 1 h at 90-100° 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 (500 mL) and washed three times with water (500 mL portions), dried over magnesium sulphate and concentrated. The resulting crude product was distilled with a bulb-to-bulb distillation (3 mBar, 121° C.) to give a colourless oil (34.7 g, gc purity 73%). The crude product was chromatographed on a silica gel column with 5% EtOAc in hexane as elution agent giving 3-(3-tert-butylphenyl)butanal (12.3 g, gc purity 99%; yield 39%).

Provenance & Evidence