Reaction equation
CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2[O:9][C:8]2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.[CH2:43]([O:46][CH2:47][CH2:48][CH2:49][CH2:50][CH:51]([CH3:53])[CH3:52])[CH:44]=[CH2:45]>C1(C)C=CC=CC=1.[Rh+]>[CH3:52][CH:51]([CH3:53])[CH2:50][CH2:49][CH2:48][CH2:47][O:46][CH2:43][CH2:44][CH2:45][CH:8]=[O:9].[CH3:45][CH:44]([CH2:43][O:46][CH2:47][CH2:48][CH2:49][CH2:50][CH:51]([CH3:53])[CH3:52])[CH:8]=[O:9]Participants
Reactant 2
Product 2
Reagents, catalysts & solvents 2
Procedure
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%).
Workup
- customfollowing purging with nitrogen
- custom1 molar ratio of hydrogen and carbon monoxide gas (30 bar, 60° C., 4 h)
- customThe reaction mixture was directly chromatographed on silica gel (hexane/diethyl ether)
- distillationdistilled
Sources & evidence
- ORD record
- ord-393579a63a764fc5ac75f66ce2ced8c1
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08088725B2
Linked notes
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