Sciencemadness Discussion Board

1-methoxy-3-vinylbenzene hydration

ItsAChitzen - 18-6-2012 at 14:20

Does it seem reasonable that the general method for anti-Markovnikov alcohol formation via B2H6 will work on 1-methoxy-3-vinylbenzene to form 3′-Methoxyacetophenone? I am broke right now, but when I get paid at the beginning of the month I will jump at the chance to experiment. If this is a total crock, or if you have papers that I should read, I would love the opportunity to learn.

kristofvagyok - 19-6-2012 at 12:54

Anti markovnikov would yield 3-methoxy-phenylethanol and not 3-methoxy phenyl-methyl-carbinol.

-do You know how does actually Markovnikov-s rule work?

With diborane and H2O2 phenylethanols will be formed and the oxidation of this will yield mainly phenylacetic acids, because the phenylacetaldehydes are really unstable....

To get to the acetophenons epoxide formation and the rearrangement of the epoxides to ketones is a much better reaction, or bromination with HBr, then hydrolisis to alcohol, then ox.

And also, orgo chem isn't as easy as it seems.

ItsAChitzen - 19-6-2012 at 13:21

Quote: Originally posted by kristofvagyok  
Anti markovnikov would yield 3-methoxy-phenylethanol and not 3-methoxy phenyl-methyl-carbinol.

Ok.
Quote:

-do You know how does actually Markovnikov-s rule work?

Yes. I want an alcohol on the least substituted carbon...
Quote:

With diborane and H2O2 phenylethanols will be formed and the oxidation of this will yield mainly phenylacetic acids, because the phenylacetaldehydes are really unstable....

To get to the acetophenons epoxide formation and the rearrangement of the epoxides to ketones is a much better reaction, or bromination with HBr, then hydrolisis to alcohol, then ox.


Fuq, I just realized I wrote the wrong product in my post. Dumb. My mistake.
Quote:

And also, orgo chem isn't as easy as it seems.


Wat? I don't think anyone is under that assumption.

[Edited on 19-6-2012 by ItsAChitzen]