[xcxo]

Make the following compound in 4 steps from benzene. Show all steps and reagents.


I'm trying to work on this question but I'm stuck on how it requires the compound to be made in only 4 steps. So far, this is what I have:

1. React the benzene with CH3Br.
2. React with Br2 and heat.
3. React with NaOH to displace the Br with -OH.
4. Friedel-Crafts acylation.
5. Reduce the carbonyl with LiAlH4.

Would anyone be able to give me a hint as to how I can produce this compound in only 4 steps instead?

[kriggy]

What if you brominated benzene first, can you then make the hydroxymethyl from bromo benzene,?