Adipoyl Chloride synthesis

I would pay attention to stoichiometry as well.

You should look up the reaction between thionyl chloride and any carboxylic acid. It's well known and very general.

Most thionyl chloride reactions are run with large excesses of thionyl chloride aka its the solvent. I usually add a drop of catalytic DMF. chlorinations like this can even work heterogeneously (the starting material not being soluble in SOCl2).