Sciencemadness Discussion Board

Anthracene

aga - 23-5-2014 at 15:10

What would be the easiest achieveable route to make Anthracene for a noob with very litle experience in C never mind OC ?

I have tried the 'Partially combusted Organic Material route', however that is very messy, yet yeilded a partial result.

The wiki says things i simply do not understand yet, i.e. 'cyclodehydration of o-methyl- or o-methylene-substituted diarylketones '


This is my 2^8 th post. Digitally significant for those with two fingers.

[Edited on 23-5-2014 by aga]

smaerd - 23-5-2014 at 16:44

What the wikipedia is saying is essentially this. The type of reaction is a 'cyclodehydration'. So likely one can imply that there will be a loss of water{dehydration} (an H2O will leave the molecule), and will form a cycle{carbon chain that closes in on itself}. The o-methyl diarylketone is a type of compound I guess you could say. The O- or P- or M- is IUPAC short-hand for Ortho, Meta, and Para regiosomers (http://en.wikipedia.org/wiki/Arene_substitution_pattern). This pertains typically but not neccesarily exclusively to benzene derivative. A ketone is a common functional group but in this case what I believe you are looking for is two benzenes bridged by a formaldehyde type functionality. My chemical drawing program says the name of this compound is, (2-methylphenyl)(phenyl)methanone.

A great website for looking up structures is - http://www.chemicalize.org/structure/#!mol=%282-methylphenyl... really helped me when learning things.

The common name for this reaction is apparently the "elbs reaction" (http://en.wikipedia.org/wiki/Elbs_reaction) . Looks like an old timey reference, K. Elbs, E. Larsen: Ueber Paraxylylphenylketon, in: Ber. Dtsch. Chem. Ges. 1884, 17, 2847–2849; doi:10.1002/cber.188401702247. Making anthracene though hmm, without that starting material, could be pretty tricky. There certainly are ways to get to that starting material though. It would take a few reactions, at least one depending on what you have available.

What are you looking to do? Do you specifically want anthracene and want to go on a synthetic adventure? Are you equipped enough to do a grignard reaction safely? Or is this a whole new world for you?


[Edited on 24-5-2014 by smaerd]

aga - 23-5-2014 at 22:13

I'm interested in Anthracence as it i an organic semiconductor, and it'd be fun to see what can be done with it.

OC is a whole new world entirely to me.

Although i may well be physically equipped to do grignard reaction, not knowing what a grignard reaction Is would be a serious drawback.

[Edited on 24-5-2014 by aga]

Lambda-Eyde - 24-5-2014 at 01:20

I think you'd be better off buying anthracene, it's not impossible to come by. Leaping into advanced organic syntheses without any previous knowledge is a bad idea. You could always get back to it after doing organic chemistry for a while.

aga - 24-5-2014 at 02:15

Agreed.

Making it is way beyond what i can do.

I will buy some as suggested.

smaerd - 24-5-2014 at 05:50

I definitely think you should buy some for now. However, I would be lying if I didn't say that it could be very fun and rewarding to try and make some yourself later down the road as a project.

Kind of like the polarimeter I am working on. I knew next to nothing about electronics before starting it. Set a goal did an appropriate amount of research, experimented now I am starting development. You can self-teach chemistry, but there are danger's/hazards, theory, and techniques which must be learned prior to attempting to do so. Either way best wishes.

aga - 24-5-2014 at 12:31

'Man's gotta know his limitations' says Clint Eastwood in some film or other.

Yes, i would be fascinated, excited, and maybe dead tinkering with totally unknowns.

At my level of understanding, it would be Science Madness to attempt it ;)