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

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

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, 201213 yr by Dr. Lennox