Synthesis of diisobutyl 3,9 perylenedicarboxylate

Im interested in making compound named diisobutyl 3,9 perylenedicarboxylate. And i have an idea but i dont know will it work. I want to make dicarboxy perylene by scholl reaction with 1 naphthoic acid and lewis acid but i dont know how to make naphthoic acid. Maybe better way is to make dicarboxy perylene from perylene itself. Then i want to esterificate it with isobuthanol.
There is picture of this compounds structure. It seems easy to make.



[Edited on 5-11-2017 by mackolol]

[Edited on 6-11-2017 by mackolol]

@ Mackolol, I have done a bit of research and it looks like there are two routes to the basic acid. The first is from 3,9-dibromo or dichloroperylene, halogen displacement to the dinitrile using cuprous cyanide (easily prepared from ferrocyanide see SM thread) and then hydrolysis of the cyano group to and acid. Or alternatively from perylene via a double Freidel-Craft acylation with acetyl chloride to 3,9-diacetylperylene and then alkaline oxidation to the required diacid.

The problem in the first case is the source of 3,9-dihaloperylenes, however, although I haven't found a definite procedure yet it appears that direct bromination in a fashion similar to the procedures for naphthalene (eg in Vogel) yields mainly the 3,9 disubstituted product. I have found a reference to the preparation of perylene from bis-(2-naphthol) which is prepapred by oxidising 2-naphthol with ferric chloride etc. The yield is low however but there may be better methods (maybe ask nicely of someone on the references thread and they will run a reaxys search for you ).

Here are a few refs about perylene to keep you busy:
Scholl et al.; Berichte C.; 1910, v43, p2203
Hansging & Zinke; Monatsh.. ; 1919; v40 p404
Zinke et al; Monatsh.. ; 1932; v61 p1
Clar; Berchte C.; 1932; v65, p846
Morgan & Mitchell; JCS; 1934; p534. (this last refs contains a reference to a simple prep for perylene but the yield is low)

For Perylene-3,9-dicarboxylic acid check out:
Pongratz; Monatsch, 1927; v 48 p585 & 1929: v52, p9
Pongratz et al.; 1933; v62 p71

Another possible route is via the degradation and reduction of perylenequinone vat dyes or perylene 3,4,9,10 tetracarboxylic acid which may partly decarboxylate at high termperatures. There are lots of patents on these two groups, most of the ones I have found so far are in German. Can you read German?

For the preparation of the tetracarboxylic acid try:
German Patents: 394794; 408513 and 412122

I have a book about the synthesis of VAT dyes and there may also be something in there. The significance of a route via perylene vat dyes is that inorder to be commercially useful it had to be easy to prepare in 1900s via a simple mix-n-bake type procedure.

Quote: Originally posted by mackolol

how can i make 1-naphthoic acid. Can somebody help me?

Quote: Originally posted by CuReUS

1.Napthalene to perylene using scholl reaction -http://onlinelibrary.wiley.com/doi/10.1002/cber.191004302175... 2.perylene to 3,9-dibromoperylene - http://onlinelibrary.wiley.com/doi/10.1002/jlac.199719970218... 3.Convert DBP to a double grignard reagent and react with dry ice to get dicarboxylic acid 4.esterification with isobutanol -http://www.tandfonline.com/doi/full/10.1080/00397911.2013.83...