Azo compound was obtained from the reaction of 4-aminophthalonitrile and thymol. After that I tried different ways to acetylation or alkyllation of free hydroxyl group. I did acetylation or alkyllation before azo coupling reaction, but it decreases azo coupled product yield and also makes the reaction more difficult.
I believe you might have tried acetic anhydride with ctalytic amount of DMAP in THF
I use cesium carbonate as alkylating base for phenols and mesylate or bromide as alkylating agent. Or make phenolates via reaction with sodium hydride. You can also add potassium iodide (0.1 eq usually) to make reaction easier. You can try to activate your carboxylic acid via coupling agents (see here https://www.omicsonline.org/open-access/peptide-coupling-reactions-2329-9053-1000e119.php?aid=43450)
You start with acetylation of toluene to get p-acetyl toluene. This is followed by nitration, reduction , diazotiszation , then coupling with other aromatic activated substrate. Direct acetylation of azocompound may not give a good results.
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