4-Acetoxybutyraldehyde → 4-Hydroxybutyl acetate
Reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH:8]=[O:9])(=[O:3])[CH3:2]>O1CCCC1>[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9])(=[O:3])[CH3:2]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
Alternatively, at least a portion of the 4-acetoxybutyraldehyde reaction product may be preferably converted to produce tetrahydrofuran (THF). Preferably, the 4-acetoxybutyraldehyde is hydrogenated to produce 4-acetoxybutanol, which then is dehydroacetoxylated to produce THF. The hydrogenation to produce 4-acetoxybutanol is preferably conducted according to the conditions described above. The 4-acetoxybutanol can then undergo a dehydroacetoxylation reaction to produce THF and acetic acid. The dehydroacetoxylation step is preferably performed at temperatures in the range of from 20 to 300° C. in the presence of a dehydroacetoxylation catalyst, such as silica, silica-alumina, and/or tungsten oxide. A final hydrolysis step may be performed to convert any 3-acetoxy-2-methylpropanol, formed by the hydrogenation of 3-acetoxy-2-methylpropionaldehyde, to 2-methyl-1,3-propanediol (MPD)
Sources & evidence
- ORD record
- ord-cbdb500bbfb1456a850aae25c2b6b105
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08124805B2
Reaction notes
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