1-Butanol → Butanal

HRID 1276846Notes

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]([O:45][CH2:41][CH2:42][CH2:43][CH3:44])[CH2:33][CH2:34][CH3:35])[CH2:38][CH2:39][CH3:40]

Participants

Reactant 5

HCID 2631-Butanol

HCID 962Water

HCID 2969Decanoic Acid

HCID 11776Triphenylphosphine

HCID 5439041-Butoxybut-2-ene

Product 2

HCID 261Butanal

HCID 222101,1-Dibutoxybutane

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 and 1.83 g (24.8 mmol) of n-butanol and stirred for 8 hours under autogeneous pressure at 155° C. Thereafter, 2.2 g (122 mmol) of water were added and stirring was continued for a further hour at 155° C. The reaction mixture was analyzed by means of calibrated gas chromatography. At a conversion of 99%, n-butyraldehyde was obtained with a selectivity of 80% and 1,1-dibutoxybutane with a selectivity of 9%.

Workup

stirringstirring
waitwas continued for a further hour at 155° C

Sources & evidence

ORD record: ord-cf8ec8408d60432d83b03dca23850b60
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06166265

Reaction notes

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