multistep synthesis question

[u2knknow]

not sure if I have this right or if in the before last step in this synthesis that NaOH is able to remove the halogen? just looking for some guidance. thx

[RajeshK]

Te second step i.e. CH3 to CH2Cl can be done using N-chloroisocyanate or can under go allylic bromination using N-Bromosuccinamide and so the Bromo will be eady to replace with NaOH

[Dr. Lennox]

Your synthesis is OK as written. Realize step 1 will produce regioisomers, however the major product will be the one you've indicated. A better route would utilize benzylic oxidation to the carboxylic acid directly via KMnO4 or H2Cr2O4 (removes two steps). The tert-butyl group will be unaffected by this oxidation since there are no hydrogens to be removed from the benzylic carbon.

Edited August 6, 2012 by Dr. Lennox