Question

Suggest a synthesis for olivetol from benzene and any necessary organic and/or inorganic reagents.

Answer 1

Olivetol is 5-Pentyl-1,3-benzenediol

You have two choices really. Do you put the C-5 chain (or something you can turn into the C-5 chain) on first then the phenol groups, or
phenol groups first, then the C-5 chain (or something you can turn into the C-5 chain).

To decide you need to think about the raction needed to put on the OH groups and the directing power of group(s) already in place
AND
what reaction is needed to put on a C-5 chain or its precursor and the directing power of OH groups.

Answer 2

Thinking of using Benzene with HNO3/H2SO4 to make Benzene with NO2 then adding Sn/Hcl/NaOH to make Benzene with NH2 then adding NaNO2/HCl/ (2) H20 to make Benzene with benzene with OH attaching at the 1, 3 position. what do you think?

Answer 3

Thinking of using Benzene with HNO3/H2SO4 to make Benzene with NO2 then adding Sn/Hcl/NaOH to make Benzene with NH2 then adding NaNO2/HCl/ (2) H20 to make Benzene with benzene with OH attaching at the 1, 3 position. what do you think?

I am thinking of putting the C-5 Group on last