As requested in
Post 486912
(silenziox: "For Antoncho", Novel Discourse), the literal transcription (this notion is essential since the original text is cryptic enough by itself
- so don't ask me for more details
):
Stage 1.Russ. J. Chem. 1958:¹17,57383
A method of oxidizing phenols to the corresponding quinolacetates is described, using minimal qtties of AcOH (sufficient for forming a paste) and Pb(AcO)4, by adding a phenol solution in a small volume of AcOH at temp <50 C; the Pb salt is filtered and from the filtrate, quinolacetates are gotten using usual methods. Thus, upon oxidation 86g ortho-cresol, there was obtained 30g 1,2-dihydro-1-methyl-2-oxophenylacetate.
Now, I understand that this part doesn’t make much sense, unfortunately, that’ all Potter provided us with – maybee we should look at the original text, which he probably hadn’t.Stage 2.Variant 1. Monatsh. Chem. 1957,88,¹3, 298-306
A variety of compounds was synthesized by condensation of 1,2-dihydro-1-Me-2-oxophenylacetate with compounds containig an active methylene group.
Thus, upon reaction of 1,2-dihydro-1-Me-2-oxophenylacetate with acetoacetic ester in presence of piperidine at 20 C, t=48h (1-2 hrs at 80-90 C), there’s formed C6H3-1-HO-2CH3-5-CH(COCH3)COOC2H5, the product is distilled at 130-140 C/0,05 mmHg.
This product was heated at 100 Ñ in 25mls 1N NaOH, yield 36%.
Variant 2.Upon reaction of 1,2-dihydro-1-Me-2-oxophenylacetate with acetylacetone in presence of piperidine at 20 Ñ the rxn proceeds for 16 hrs (10mins at 100 C). The product, C6H3-1-HO-2CH3-5-CH(COCH3)2 is distilled at 115-120/0,05 mmHg. Yield = 89%
0,55 g of the above product was heated in 5mls 10% aq. NaOH for 2hrs at 100 C. Yeild of 4-Me-3-OH-P2P comprised 71%. B.p. – 110-120 Ñ (èôåð temperature) at 0,05 mmHg.
So…. here goes
The chemistry is absolutely weird for us, the Hive Bees, and there’s not much details.
Anyway, I hope you found it interesting, although there’s very little hope that someone here will ever embark onto this synthetic route
I think it’d bee much more useful if someone could get those refs, won’t it?
Yours,
Antoncho