[amr6257]

So I am working through a synthesis problem, trying to get to phenyl-1-propanone.  I have come up with a partial method and I appear to be stuck.

So I did a hydration of ethylbenzene to 1-phenyl-1-ethanol (H2O + H+).
Then converted the alcohol group to a ketone using Na2Cr2O7, H2SO4, H2O.
Then, I still need to add a carbon to my chain and thought to do a grignard reaction.  However I ended up with 1-phenyl-2-hydroxy-propan-1-one.  So I just need to get the OH group to leave.  I have a couple ideas but I don't know how they work with my ketone.   I also know OH isn't the best leaving group.  Isn't there a way to reduce alcohols?  Will that interact with the ketone.  Can I use OHCH2CH2OH to make an acetal to act as a protecting group for the ketone?

I am sure there is a simpler method that I am missing too.  Any suggestions would be appreciated.

[AromaticAcrobatic]

Yeah so that chromic acid step probably wouldn't give the intermediate you'd be after in your proposal. But we can use it in our favor.
1) Na2Cr2O7, H2SO4, H2O
2) SOCl2
3) LiAl(OR3)H then H2O ( R = ethyl)
3!= product

 

[discodermolide]

So how do you get from ethylbenzene

to

with aqueous acid?

Do you mean the starting material is styrene?

[orgopete]

So I am working through a synthesis problem, trying to get to phenyl-1-propanone.  I have come up with a partial method and I appear to be stuck.

So I did a hydration of ethylbenzene to 1-phenyl-1-ethanol (H2O + H+).
Then converted the alcohol group to a ketone using Na2Cr2O7, H2SO4, H2O.
Then, I still need to add a carbon to my chain and thought to do a grignard reaction.  However I ended up with 1-phenyl-2-hydroxy-propan-1-one.  So I just need to get the OH group to leave.  I have a couple ideas but I don't know how they work with my ketone.   I also know OH isn't the best leaving group.  Isn't there a way to reduce alcohols?  Will that interact with the ketone.  Can I use OHCH2CH2OH to make an acetal to act as a protecting group for the ketone?

I am sure there is a simpler method that I am missing too.  Any suggestions would be appreciated.

Huh? A lot looks wrong here. Could you draw out your scheme, take a photo, and attach it to your post? (I would not be surprised that the process of doing this may result it in your catching some of the errors.)