Step 1: Alkylate toluene with chloroacetone, to get p-toluacetone
It would be called p-Tolylacetone.
Using benzene/chloroacetone the yield is 32% P2P - https://www.thevespiary.org/rhodium/Rhodium/chemistry/phenylacetone.html#chloroacetone (https://www.thevespiary.org/rhodium/Rhodium/chemistry/phenylacetone.html#chloroacetone)
Here you have a few 1,2-dihydroxybenzene methylenations. (https://www.thevespiary.org/rhodium/Rhodium/chemistry/methylenation.html#methylenation)
(https://www.thevespiary.org/rhodium/Rhodium/chemistry/methylenation.html#methylenation)
Unfortunately, the only method of creating that bridge is to use a dihalomethane and a base, you cannot make a formaldehyde acetal with 1,2-dihydroxybenzenes like you can with alcohols, as phenols do not react like aliphatic alcohols.
This is one of the reasons why it is necessary to go through the literature to see what kind of reactions are actually possible in practice, and not what seems good on paper. A few hours in the library often saves many days of work in the lab.
why, at the rate ning has been spending time in the library, ning might not even have to go to the lab...
Upon rethinking, and mild what-we-all-hope-is-sucess in the lab, ning has rethought the beginning of this synth, and thought it to be better this way:
step 1: toluene nitration a la rhodium (https://www.thevespiary.org/rhodium/Rhodium/chemistry/aromatic.nitration.html)
(https://www.thevespiary.org/rhodium/Rhodium/chemistry/aromatic.nitration.html)
if this step has the claimed 84% ortho selectivity, we're in business.
Step 2: reduction of o-nitrotoluene to o-aminotoluene
this is well covered, thinks ning. Zinc dust, iron dust, HCl, rhodium has something on it, etc.
Step 3: oxidation of o-aminotoluene to o-toluquinone (https://www.thevespiary.org/rhodium/Rhodium/chemistry/benzoquinone.html)
(https://www.thevespiary.org/rhodium/Rhodium/chemistry/benzoquinone.html)
ning's favorite MnO2 will probably work here also, as the book said so, and ning believes everything ning reads. Especially on the net... ;)
All you expert bees know how to take it from here (https://www.thevespiary.org/rhodium/Rhodium/chemistry/stp.html)
(https://www.thevespiary.org/rhodium/Rhodium/chemistry/stp.html)...
The advantage of this method is:
1. from toluene, it might bee higher yielding than trying to get the p-nitrotoluene out from mixed nitration isomers. 84%, wow...
Or at least, it could be easier to separate isomers by just using the cleanup between procedures to weed them out.
Dear Ning!
Lego really likes your enthusiasm and your ideas, but there are still some problems.
The oxidation of 2-aminotoluene with MnO2/H2SO4 will yield not only the desired methylbenzoquinone but also the methyl-group will be oxidized to the aldehyde or even to the benzoic acid. See Post 208702 (https://www.thevespiary.org/talk/index.php?topic=7285.msg20870200#msg20870200)
(Antoncho: "The easiest synth of benzaldehyde from toluene", Chemistry Discourse).
MnO2 is OTC, not only in batteries. It is used and sold as a pigment for oil paintings. The puritiy is only technical but for oxidation of such a simple molecule it should work.