You could use an alcohol as the solvent? That should dissolve both the alkene and the NaOH.
Thank you. I also found a paper that describes the dihydroxylation of alkene using a tertiary alcohol or acetone as solvent. Maybe I should try acetone first.
You could use an alcohol as the solvent? That should dissolve both the alkene and the NaOH.
Thank you. I also found a paper that describes the dihydroxylation of alkene using a tertiary alcohol or acetone as solvent. Maybe I should try acetone first.
For my information: would the alkene react with H2O2 to make the diol, or with N2O to make the epoxy, as vapours, diluted in N2 to avoid a flame? Apologies for interrupting.
For my information: would the alkene react with H2O2 to make the diol, or with N2O to make the epoxy, as vapours, diluted in N2 to avoid a flame? Apologies for interrupting.
Looking at the TLC, I don't think you have converted the alkene to the diol or the acid. The difference in polarity should be starkly different with either of those products from the starting material.
Looking at the TLC, I don't think you have converted the alkene to the diol or the acid. The difference in polarity should be starkly different with either of those products from the starting material.
You might want to use Milas or Upjohn dihydroxilations with OsO4 https://en.wikipedia.org/wiki/Milas_hydroxylation https://en.wikipedia.org/wiki/Upjohn_dihydroxylation
Maybe there are other methods Sharpless hydroxilation maybe?
I never did any of those so Im not sure if they work in other solvents than water but if you find oxidant soluble in organic solvent then you should be good
Thank you.. but there are some difficulty to order Osmium Tetroxide in my place and I would like to try a simpler and safe method first.
You might want to use Milas or Upjohn dihydroxilations with OsO4 https://en.wikipedia.org/wiki/Milas_hydroxylation https://en.wikipedia.org/wiki/Upjohn_dihydroxylation
Maybe there are other methods Sharpless hydroxilation maybe?
I never did any of those so Im not sure if they work in other solvents than water but if you find oxidant soluble in organic solvent then you should be good
Thank you.. but there are some difficulty to order Osmium Tetroxide in my place and I would like to try a simpler and safe method first.
I just checked the NMR of the product, and I think the alkene is over oxidized and the product could possibly be a carboxylic acid (I submitted a sample for mass spectrometry analysis to confirm). The image below is the TLC of the starting material and right after the reaction for 30 minutes at room temperature.
If I lower the reaction temperature, my substrate may easily precipitate from the solvent since it is not very soluble in acetonitrile. Shall I change the solvent or I should employ another method now?
I just checked the NMR of the product, and I think the alkene is over oxidized and the product could possibly be a carboxylic acid (I submitted a sample for mass spectrometry analysis to confirm). The image below is the TLC of the starting material and right after the reaction for 30 minutes at room temperature.
If I lower the reaction temperature, my substrate may easily precipitate from the solvent since it is not very soluble in acetonitrile. Shall I change the solvent or I should employ another method now?
It seems that there was something happening using Acetonitrile as solvent, and potassium permanganate solution. I can see another spot appeared in the TLC.
The new spot in TLC showed that it is soluble in chloroform, I then used chloroform and did a liquid-liquid extraction. I collected the chloroform solution, and removed chloroform usinf the rovap. I then obtained a power that is insoluble in everything! I did the TLC again and then spot disappeared. Is the 1,2-diol so reactive that it formed polymers (polyethers) with chloroform? I think I will try to use ethyl acetate again next time.
It seems that there was something happening using Acetonitrile as solvent, and potassium permanganate solution. I can see another spot appeared in the TLC.
The new spot in TLC showed that it is soluble in chloroform, I then used chloroform and did a liquid-liquid extraction. I collected the chloroform solution, and removed chloroform usinf the rovap. I then obtained a power that is insoluble in everything! I did the TLC again and then spot disappeared. Is the 1,2-diol so reactive that it formed polymers (polyethers) with chloroform? I think I will try to use ethyl acetate again next time.
There is another example I found on the internet about alkene oxidation. The example is a vinyl compound (same case as mine) and here is the quoted text:
"In basic conditions, treatment of alkene with potassium permanganate forms a vicinal diol. Oxidative cleavage by permanganate in neutral or acidic conditions, however, leads to cleavage to form carbonyl compounds by means of the same cyclic manganate ester intermediate. Where ozonolysis, another method of oxidative cleavage of alkenes, produces an aldehyde or formaldehyde, cleavage with permanganate produces a carboxylic acid or carbon dioxide respectively. "
Reference is here: http://www.wikipremed.com/03_organicmechanisms.php?mch_code=030202_080
There is another example I found on the internet about alkene oxidation. The example is a vinyl compound (same case as mine) and here is the quoted text:
"In basic conditions, treatment of alkene with potassium permanganate forms a vicinal diol. Oxidative cleavage by permanganate in neutral or acidic conditions, however, leads to cleavage to form carbonyl compounds by means of the same cyclic manganate ester intermediate. Where ozonolysis, another method of oxidative cleavage of alkenes, produces an aldehyde or formaldehyde, cleavage with permanganate produces a carboxylic acid or carbon dioxide respectively. "
Reference is here: http://www.wikipremed.com/03_organicmechanisms.php?mch_code=030202_080
OH! I just read Wikipedia about some basic Organic Chemsitry I alkene oxidation with KMNO4, I performed my reaction in a neutral condition. I think I shall do one reaction in basic condition. I totally forgot how different the products would be under different pH for an alkene oxidation with permanganate.
OH! I just read Wikipedia about some basic Organic Chemsitry I alkene oxidation with KMNO4, I performed my reaction in a neutral condition. I think I shall do one reaction in basic condition. I totally forgot how different the products would be under different pH for an alkene oxidation with permanganate.
You might want to use Milas or Upjohn dihydroxilations with OsO4 https://en.wikipedia.org/wiki/Milas_hydroxylation https://en.wikipedia.org/wiki/Upjohn_dihydroxylation
Maybe there are other methods Sharpless hydroxilation maybe?
I never did any of those so Im not sure if they work in other solvents than water but if you find oxidant soluble in organic solvent then you should be good
You might want to use Milas or Upjohn dihydroxilations with OsO4 https://en.wikipedia.org/wiki/Milas_hydroxylation https://en.wikipedia.org/wiki/Upjohn_dihydroxylation
Maybe there are other methods Sharpless hydroxilation maybe?
I never did any of those so Im not sure if they work in other solvents than water but if you find oxidant soluble in organic solvent then you should be good
http://www.organic-chemistry.org/namedreactions/prevost-reaction.shtm
I've had reasonable success with the catalytic version, with periodate as the terminal oxidant (Org. Lett., 2005, 7, 5071).
http://www.organic-chemistry.org/namedreactions/prevost-reaction.shtm
I've had reasonable success with the catalytic version, with periodate as the terminal oxidant (Org. Lett., 2005, 7, 5071).
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Thank you. I also found a paper that describes the dihydroxylation of alkene using a tertiary alcohol or acetone as solvent. Maybe I should try acetone first.
Thank you. I also found a paper that describes the dihydroxylation of alkene using a tertiary alcohol or acetone as solvent. Maybe I should try acetone first.
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Apologies for interrupting.
Apologies for interrupting.
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Thank you.. but there are some difficulty to order Osmium Tetroxide in my place and I would like to try a simpler and safe method first.
Thank you.. but there are some difficulty to order Osmium Tetroxide in my place and I would like to try a simpler and safe method first.
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Did you run the plate in straight Chloroform or a mixed eluent ?
What are the Rf values of the alkene and the new spot ?
Did you run the plate in straight Chloroform or a mixed eluent ?
What are the Rf values of the alkene and the new spot ?
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If I lower the reaction temperature, my substrate may easily precipitate from the solvent since it is not very soluble in acetonitrile. Shall I change the solvent or I should employ another method now?
If I lower the reaction temperature, my substrate may easily precipitate from the solvent since it is not very soluble in acetonitrile. Shall I change the solvent or I should employ another method now?
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The new spot in TLC showed that it is soluble in chloroform, I then used chloroform and did a liquid-liquid extraction. I collected the chloroform solution, and removed chloroform usinf the rovap. I then obtained a power that is insoluble in everything! I did the TLC again and then spot disappeared.
Is the 1,2-diol so reactive that it formed polymers (polyethers) with chloroform?
The new spot in TLC showed that it is soluble in chloroform, I then used chloroform and did a liquid-liquid extraction. I collected the chloroform solution, and removed chloroform usinf the rovap. I then obtained a power that is insoluble in everything! I did the TLC again and then spot disappeared.
Is the 1,2-diol so reactive that it formed polymers (polyethers) with chloroform?
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The example is a vinyl compound (same case as mine) and here is the quoted text:
"In basic conditions, treatment of alkene with potassium permanganate forms a vicinal diol. Oxidative cleavage by permanganate in neutral or acidic conditions, however, leads to cleavage to form carbonyl compounds by means of the same cyclic manganate ester intermediate. Where ozonolysis, another method of oxidative cleavage of alkenes, produces an aldehyde or formaldehyde, cleavage with permanganate produces a carboxylic acid or carbon dioxide respectively. "
Reference is here: http://www.wikipremed.com/03_organicmechanisms.php?mch_code=030202_080
The example is a vinyl compound (same case as mine) and here is the quoted text:
"In basic conditions, treatment of alkene with potassium permanganate forms a vicinal diol. Oxidative cleavage by permanganate in neutral or acidic conditions, however, leads to cleavage to form carbonyl compounds by means of the same cyclic manganate ester intermediate. Where ozonolysis, another method of oxidative cleavage of alkenes, produces an aldehyde or formaldehyde, cleavage with permanganate produces a carboxylic acid or carbon dioxide respectively. "
Reference is here: http://www.wikipremed.com/03_organicmechanisms.php?mch_code=030202_080
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I performed my reaction in a neutral condition. I think I shall do one reaction in basic condition. I totally forgot how different the products would be under different pH for an alkene oxidation with permanganate.
I performed my reaction in a neutral condition. I think I shall do one reaction in basic condition. I totally forgot how different the products would be under different pH for an alkene oxidation with permanganate.
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https://en.wikipedia.org/wiki/Milas_hydroxylation
https://en.wikipedia.org/wiki/Upjohn_dihydroxylation
Maybe there are other methods Sharpless hydroxilation maybe?
I never did any of those so Im not sure if they work in other solvents than water but if you find oxidant soluble in organic solvent then you should be good
https://en.wikipedia.org/wiki/Milas_hydroxylation
https://en.wikipedia.org/wiki/Upjohn_dihydroxylation
Maybe there are other methods Sharpless hydroxilation maybe?
I never did any of those so Im not sure if they work in other solvents than water but if you find oxidant soluble in organic solvent then you should be good
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