1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → 4-[(5-Methylhexyl)oxy]butanal

Participants

Reaction Steps

Acetylacetanatodicarbonyl rhodium (I) (0.005 g, 0.02 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.030 g, 0.05 mmol) were added to a 25 mL glass-lined autoclave and dissolved in toluene (3 mL). 1-(allyloxy)-5-methylhexane (2.0 g, 12.2 mmol) was added to the reactor and, following purging with nitrogen, the reaction mixture was subjected to hydroformylation conditions using a 1:1 molar ratio of hydrogen and carbon monoxide gas (30 bar, 60° C., 4 h) with vigorous stirring. The reaction mixture was directly chromatographed on silica gel (hexane/diethyl ether). The isolated products were Kugelrolhr distilled to give 4-[(5-methylhexyl)oxy]butanal (1.4 g, 7.5 mmol, chemical yield 62%) and 2-methyl-3[(5-methylhexyl)oxy]propanal (0.14 g, 6.2%).

Provenance & Evidence