Triphenyl phosphite → 3-(1,1-Dimethylethyl)benzenepropanal

Participants

Reaction Steps

Acetylacetonatodicarbonylrhodium (I) (41 mg, 0.1 mol %) of 1-tert-butyl-3-vinylbenzene (29 g, 0.16 mol) and a solution of triphenylphosphite (261 mg, 0.99 mmol) in 88 g of toluene were added to a 250 mL autoclave vessel. The vigorously stirred reaction mixture heated for 6 h under a pressure of syn gas (mixture of hydrogen and carbon monoxide in a ratio 1:1-1 Bar), at 80° C. The crude reaction mixture was concentrated in vacuo and chromatographed on a silica gel column with 3% MTBE in hexane as elution agent to give 3-(3-tert-butylphenyl)propanal (24.5 g, gc purity>82%; yield=63%).

Provenance & Evidence