What is phenol?

Addition of alkyl groups to phenol

• I'm looking for a plausible synthesis for 2,5 (alkyl)phenol. Having trouble with a question in an organic chemistry textbook I'm studying. hydoxyl groups appear to be ortho-para directing, so the first addition would result in an even mix of ortho and para alkyl phenol, and the second addition would result in a mix of ortho-para and the desired ortho-ortho product, with yeild of the ortho-ortho form being very low. I'm looking for a synthesis that results mostly in the formation of the ortho-ortho form. Consider other initial reactants than phenol, and the addition of other groups besides alkyl as reaction intermediates. The question hints that the sequence of reactants is important. I'm not sure I'm using the proper nomenclature for the location, so to clarify, I wish a phenol molecule with two alkyl groups, one on either side of the hydroxyl on the benzene ring. It shouldn't be neccesary to provide details of the specific reactions neccesary to attach the alkyl or other groups, but names of the reactions would be helpful, as in "attach the alkyl group by freidel-krafts alkylation", or "chlorinate with FeCl3 and Cl2".

• Answer:

  Ok, I will give it a shot, if you are not happy then feel free to resubmit. I am not an organic chemistry major and in fact have not done any chemistry since, well a long time ago. I am not really sure what you are trying to make but with the help of our ever favorite Google search engine I came up with a few sites that might answer your question or at least point you in the right direction. This page is called the Index for Organic Chemistry Online and it includes practice questions: http://www.cem.msu.edu/~reusch/OrgPage/VirtualText/intro1b.htm Dr. David Woodcock at the Okanagan University College has this page with a lot of good stuff: http://people.ouc.bc.ca/woodcock/molecule/molecule.html Then there is 11th hour Organic Chemistry I&II: http://www.blackwellscience.com/11thhour/book6/oc2ch3.html Again I am not entirely sure of what exactly you are looking for but these at least looked like a good place to start. By using complex search terms, sometimes you can tease out a website with just exactly what you want. In this case the terms I used were: organic chemistry phenols Organic Chemistry 2,6 (alkyl)phenol Approx. 2800 hits so I am sure that one of those will get you what you need.