[imjonk]

Hello all, new to the forum.  I'm working on an advanced ochem experiment to get from benzyl alcohol to p-cresol.  i'm stumped on this.

I am trying to figure out a reaction from benzyl alcohol to p-cresol.  i know how to go from p-cresol to benzyl alcohol, but i can't figure out the best way for the reverse.  

One way i've looked at it is going from benzyl alcohol to toluene somehow, then sulfonation of the toluene followed by NaOH and heat to end with the cresol.

Direct answers are appreciated, but any tips or nudges in the right direction would be most helpful.  Thanks!

[karvon]

You could make a benzyl ester and then hydrogenate it to toluene on a palladium catalyst.

[saden99]

Edit: Wow...nevermind wasn't thinking. Will be a second after this edit.

[discodermolide]

Hello all, new to the forum.  I'm working on an advanced ochem experiment to get from benzyl alcohol to p-cresol.  i'm stumped on this.

I am trying to figure out a reaction from benzyl alcohol to p-cresol.  i know how to go from p-cresol to benzyl alcohol, but i can't figure out the best way for the reverse.  

One way i've looked at it is going from benzyl alcohol to toluene somehow, then sulfonation of the toluene followed by NaOH and heat to end with the cresol.

Direct answers are appreciated, but any tips or nudges in the right direction would be most helpful.  Thanks!

So how do you get from o-cresol to benzyl alcohol? Have you got your nomenclature correct?
Perhaps you could draw us a scheme for this reaction. Because I see no simple way to go from o-cresol to benzyl alcohol.

[imjonk]

Oh, i'll look into that karvon, thanks!

@disco
i didn't get any firm procedures on how to do it, but from the information i found you can get from toluene from cresol by distilling with zinc.  To get to the benzyl alcohol you can chlorinate to phenyl chloromethane then NaOH to complete.  Of course isolating/distilling/crystallizing between all the steps.  This process is also may not be 100 percent, but i stated that mostly to make the point that it seemed easier to find ways to go in reverse.  And not sure if you're confused or the font looks strange, but i said p-cresol, not ortho-.  Though i think either way the process i mentioned should still work according to the scientists somewhere.

[discodermolide]

Zinc is a reducing agent  and you require oxygen to be able to do this, I think not! And how do you chlorinate, with what?

Toluene can be made from cresol by zinc distillation, a quote from Wikipedia "In Chemistry, Cresols can be used to synthesise Toluene. When cresol (o-, m-, p-)is distilled with zinc dust, toluene is obtained."

[imjonk]

Hmm... i think this topic is digressing quite a bit.  My main question was starting from a benzyl alcohol and reacting with reagents to create p-cresol and that still stands.  And @disco:  i'm not sure what your line of questioning does for my cause unless you feel that you want to synthesize some benzyl alcohol.  In which case, i feel like this is the wrong thread for you and i'd definitely be the last person to ask for advice on how to do that.

[macman104]

What if you could get to the p-bromophenol (or a derivate if the phenol is troublesome) and performing stille coupling with methylstannane?

[orgopete]

I am not motivated to answer this question because I don't know the real question. This cannot be how to convert benzyl alcohol to cresol, can it? Your suggested route is one of many that would work, though you have selected a more brutal set of conditions, but it is reasonably short and would presumably work. So, unless you have something more convincing to add, I say buy it.

[discodermolide]

I am not motivated to answer this question because I don't know the real question. This cannot be how to convert benzyl alcohol to cresol, can it? Your suggested route is one of many that would work, though you have selected a more brutal set of conditions, but it is reasonably short and would presumably work. So, unless you have something more convincing to add, I say buy it.

I feel the same.
I wanted to know what his perceived conditions for the route from cresol to benzyl alcohol were, as the original posts were somewhat confusing.

[imjonk]

My apologies for making it confusing (and unmotivating).

i require assistance for the reaction:
benzyl alcohol ->  p-cresol

a multi-step synthesis would be acceptable, but i am doing this for a college lab so it has to be something that won't kill me or excessively toxic chemicals.  Exact procedures are not necessary because it's not like I don't want to do the legwork.  I've tried using scifinder and my organic text without significant progress.

One reason I looked at toluene as a part of the synthesis was because I found a way to react the toluene with hydrogen peroxide, copper nitrate, Na₂HPO₄, KH₂PO₄, acetonitrile, and water to get p-cresol.  But I couldn't find exact amounts so still trying to figure that out as a possibility.

And disco, sorry for getting confusing, but the cresol is the final product.  not starting.

[SVXX]

What reagents do you have?
You could try oxidizing it to benzoic acid, decarboxylating and starting off on benzene.