Reaktion #502071

Reaktionsgleichung

1-(allyloxy)-5-methylhexane

(9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine)

→

2-methyl-3[(5-methylhexyl)oxy]propanal

Ausbeute 6.2%

4-[(5-methylhexyl)oxy]butanal

Ausbeute 62.0%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigefollowing purging with nitrogen
2. 2
   Sonstige1 molar ratio of hydrogen and carbon monoxide gas (30 bar, 60° C., 4 h)
3. 3
   SonstigeThe reaction mixture was directly chromatographed on silica gel (hexane/diethyl ether)
4. 4
   workup.DISTILLATIONdistilled

Vorschrift

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%).

Quelle