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3-step process to make propyl ethanoate from propene
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Kevin Thorpe
3-step process to make propyl ethanoate from propene
My proposal is hydroboration followed by Fischer esterification. It's 2 or 3 steps depending on how many you count hydroboration to be.
Alternatively if you are intent on going through a haloalkane pathway, you could try anti-Markovnikov addition of $\ce{HBr}$ by reacting it in the presence of $\ce{H2O2}$ to prepare 1-bromopropane. Then you could do nucleophilic substitution of $\ce{OH-}$ followed by Fischer esterification. This method would have a lower yield though due to the competing E2 reaction.
My proposal is hydroboration followed by Fischer esterification. It's 2 or 3 steps depending on how many you count hydroboration to be.
Alternatively if you are intent on going through a haloalkane pathway, you could try anti-Markovnikov addition of $\ce{HBr}$ by reacting it in the presence of $\ce{H2O2}$ to prepare 1-bromopropane. Then you could do nucleophilic substitution of $\ce{OH-}$ followed by Fischer esterification. This method would have a lower yield though due to the competing E2 reaction.
is. Special conditions by which an acid ($\ce{HBr}$) adds to the alkene to form a primary haloalkane, which can then be used to form the primary alcohol.More
@DefinitelyNotAPlesiosaur with ChemDraw. And its two steps if you consider the entirety of hydroboration as one step, or three if you consider borane addition and $\ce{NaOH}$ and $\ce{H2O2}$ addition as separate steps. If you dont want to use my proposed one, the alternative one is definitely three steps.More
Essentially, I need to get a primary alcohol from an alkene. Do you think that I could do this with electrophilic addition in some special solution (like a protic solution) or in some special conditions (like extreme temperature)?More
Esterify. The typical Fischer esterification (with carboxylic acid and concentrated sulfuric acid) should probably work, although there are many other possibilities. One is to use the acyl chloride with a weak base. The weak base serves as a nucleophilic catalyst, and also helps to mop up the $\ce{HCl}$ produced in the reaction. A common choice is 4-dimethylaminopyridine, often called DMAP. Another option is to use the carboxylic acid with dicyclohexylcarbodiimide (DCC) and DMAP. The DCC activates the carboxylic acid in what is known as the Steglich esterification.
Reduce the double bond by catalytic hydrogenation. C=C double bonds are generally more susceptible to catalytic hydrogenation than C=O double bonds (disclaimer: this may vary depending on the catalyst and conditions chosen), so this reaction can proceed chemoselectively to give the desired product, n-propyl acetate:
Esterify. The typical Fischer esterification (with carboxylic acid and concentrated sulfuric acid) should probably work, although there are many other possibilities. One is to use the acyl chloride with a weak base. The weak base serves as a nucleophilic catalyst, and also helps to mop up the $\ce{HCl}$ produced in the reaction. A common choice is 4-dimethylaminopyridine, often called DMAP. Another option is to use the carboxylic acid with dicyclohexylcarbodiimide (DCC) and DMAP. The DCC activates the carboxylic acid in what is known as the Steglich esterification.
Reduce the double bond by catalytic hydrogenation. C=C double bonds are generally more susceptible to catalytic hydrogenation than C=O double bonds (disclaimer: this may vary depending on the catalyst and conditions chosen), so this reaction can proceed chemoselectively to give the desired product, n-propyl acetate:
My proposal is hydroboration followed by Fischer esterification. It's 2 or 3 steps depending on how many you count hydroboration to be.
Alternatively if you are intent on going through a haloalkane pathway, you could try anti-Markovnikov addition of $\ce{HBr}$ by reacting it in the presence of $\ce{H2O2}$ to prepare 1-bromopropane. Then you could do nucleophilic substitution of $\ce{OH-}$ followed by Fischer esterification. This method would have a lower yield though due to the competing E2 reaction.
My proposal is hydroboration followed by Fischer esterification. It's 2 or 3 steps depending on how many you count hydroboration to be.
Alternatively if you are intent on going through a haloalkane pathway, you could try anti-Markovnikov addition of $\ce{HBr}$ by reacting it in the presence of $\ce{H2O2}$ to prepare 1-bromopropane. Then you could do nucleophilic substitution of $\ce{OH-}$ followed by Fischer esterification. This method would have a lower yield though due to the competing E2 reaction.
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Here's another way.
Oxidise propene to prop-2-en-1-ol with selenium dioxide. Here's a reference: J. Org. Chem., 1979, 44, 4683
Esterify. The typical Fischer esterification (with carboxylic acid and concentrated sulfuric acid) should probably work, although there are many other possibilities. One is to use the acyl chloride with a weak base. The weak base serves as a nucleophilic catalyst, and also helps to mop up the $\ce{HCl}$ produced in the reaction. A common choice is 4-dimethylaminopyridine, often called DMAP. Another option is to use the carboxylic acid with dicyclohexylcarbodiimide (DCC) and DMAP. The DCC activates the carboxylic acid in what is known as the Steglich esterification.
Reduce the double bond by catalytic hydrogenation. C=C double bonds are generally more susceptible to catalytic hydrogenation than C=O double bonds (disclaimer: this may vary depending on the catalyst and conditions chosen), so this reaction can proceed chemoselectively to give the desired product, n-propyl acetate:
Here's another way.
Oxidise propene to prop-2-en-1-ol with selenium dioxide. Here's a reference: J. Org. Chem., 1979, 44, 4683
Esterify. The typical Fischer esterification (with carboxylic acid and concentrated sulfuric acid) should probably work, although there are many other possibilities. One is to use the acyl chloride with a weak base. The weak base serves as a nucleophilic catalyst, and also helps to mop up the $\ce{HCl}$ produced in the reaction. A common choice is 4-dimethylaminopyridine, often called DMAP. Another option is to use the carboxylic acid with dicyclohexylcarbodiimide (DCC) and DMAP. The DCC activates the carboxylic acid in what is known as the Steglich esterification.
Reduce the double bond by catalytic hydrogenation. C=C double bonds are generally more susceptible to catalytic hydrogenation than C=O double bonds (disclaimer: this may vary depending on the catalyst and conditions chosen), so this reaction can proceed chemoselectively to give the desired product, n-propyl acetate:
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