1-Butanol → Butanal

HRID 1276847Notes

Reaction equation

HRID 1276847 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20](O)(=[O:30])[CH2:21][CH2:22][CH2:23]CCCCCC.[CH2:32]([O:36][CH2:37][CH:38]=[CH:39][CH3:40])[CH2:33][CH2:34][CH3:35].[CH2:41]([OH:45])[CH2:42][CH2:43][CH3:44].O>>[CH:20](=[O:30])[CH2:21][CH2:22][CH3:23].[CH2:37]([O:36][CH:32]=[CH:33][CH2:34][CH3:35])[CH2:38][CH2:39][CH3:40].[CH2:37]([O:36][CH:32]([O:45][CH2:41][CH2:42][CH2:43][CH3:44])[CH2:33][CH2:34][CH3:35])[CH2:38][CH2:39][CH3:40]

Participants

8

Reactant 5

HCID 2631-ButanolHCID 962WaterHCID 2969Decanoic AcidHCID 11776TriphenylphosphineHCID 5439041-Butoxybut-2-ene

Product 3

HCID 261ButanalHCID 222101,1-DibutoxybutaneHCID 347145HCID 347145, compound

Conditions

Temperature
155 °C

Procedure

A glass autoclave was filled with 0.022 g of the catalyst HRuCl(CO)(PPh3)3, 0.031 g of triphenylphosphine, 0.005 g of decanoic acid, 3.18 g (24.8 mmol) of 1-butoxybut-2-ene, 1.83 g (24.8 mmol) of n-butanol and 2.2 g (122 mmol) of water and stirred for 16 hours under autogenous pressure at 155° C. The reaction mixture was analyzed by means of calibrated gas chromatography. At a conversion of 48%, n-butyraldehyde was obtained with a selectivity of 80%, 1-butoxybut-1-ene with a selectivity of 10% and 1,1-dibutoxybutane with a selectivity of 0.3%.

Sources & evidence

ORD record
ord-66fb1c0f89e441edaf9740759ff855c3
Source dataset
uspto-grants-2000_12
Patent number
US06166265

Reaction notes

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