Butanal → HCID 131731839, compound

HRID 74121Notes

Reaction equation

[CH:1](=[O:5])[CH2:2][CH2:3][CH3:4].[CH2:6]([OH:10])[CH:7]([OH:9])[CH3:8]>[Pd]>[CH:1](=[O:5])[CH2:2][CH2:3][CH3:4].[CH2:6]([OH:10])[CH:7]([OH:9])[CH3:8]

Participants

Conditions

Temperature: 180 °C

Procedure

n-Butyraldehyde (3.6 g, 4.5 ml; 0.05 mol), 1,2-propanediol (76.1 g, 73.4 ml; 1 mol), and 0.18 g of 10% Pd/C (5 wt % to n-butyraldehyde) are charged to a 150 ml Parr reactor. The system is purged with nitrogen three times. Then 500 psi of hydrogen is charged, the reactor is heated to 180° C., and the hydrogen pressure is adjusted to 1000 psi. After 3 hours at 180° C. and 1000 psi, GC analysis shows complete conversion of n-butyraldehyde and formation of an approximately 1:1 mixture of 2-butoxy-1-propanol and 1-butoxy-2-propanol (79.2%), n-butanol (5.8%), and cis/trans 2-propyl-4-methyl-1,3-dioxolane (11.9%).

Workup

customThe system is purged with nitrogen three times
additionThen 500 psi of hydrogen is charged
additionconversion of n-butyraldehyde and formation of an approximately 1:1 mixture of 2-butoxy-1-propanol and 1-butoxy-2-propanol (79.2%), n-butanol (5.8%), and cis/trans 2-propyl-4-methyl-1,3-dioxolane (11.9%)

Sources & evidence

ORD record: ord-b4c185c0de19400b82302d03b7607c44
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08829229B2

Reaction notes

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