PiperonylIC acid

Supplement 1952 2666-3031 Carbonyl compounds Ethylene carbonate, 100. Piperonal, 116. Thioindigo, 177. Fluorescein, 222. Carboxylic acids Piperonylic acid, 269. Amines, 328. Three Cyclic Oxygens, 381. Four Cyclic Oxygens, 433. Fiite Cyclic Oxygens, 459.. . . ... 

I ve found that unfortunately, there is a hyper oxydation of oleofin as side reaction, and gives organic acids, probably MDPhenylace-tic acid and may be a bit of piperonylic acid. It s easy to realise it. 

METHOD 6 This one is for meth cooks only as it is only practical for making P2P, not MD-P2P because Strike don t know where one can get piperonylic acid . It has been around awhile and works really well [20]. Therefore the chemicals needed have been restricted for quite some time. But if one can get them then what the hell. 

This is a way to do this procedure without having to use one of those crazy tube furnaces stuffed with thorium oxide or manganous oxide catalyst [21]. The key here is to use an excess of acetic anhydride. Using even more than the amount specified will insure that the reaction proceeds in the right direction and the bad side reaction formation of dibenzylketone will be minimalized (don t ask). 18g piperonylic acid or 13.6g phenylacetic acid, 50mL acetic anhydride and 50mU pyridine are refluxed for 6 hours and the solvent removed by vacuum distillation. The remaining residue is taken up in benzene or ether, washed with 10% NaOH solution (discard the water layer), and vacuum distilled to get 8g P2P (56%). 

METHOD 7 Another piperonylic acid method for your perusal [22, 23]. 70g piperonylic acid or 65g phenylacetic acid in 250mL DCM is stirred in a flask and 64g SOCb is added dropwise. The solution is heated to reflux until no more HCI gas is released from the solution. The chemist should have a tube leading from the top of the reflux condenser to a glass of water to catch all that HCI... 

Isosafrol yields piperonal (heliotropine) melting at 37° as the principal product of oxidation when potassium permanganate is used as the oxidising agent. If the oxidation be very energetic piperonylic acid, melting at 228°, is the principal reaction product. 

Phenylhydrazine, 113 /3-Phenylhvdroxylamine, 113 Piperonal, 82 Piperonylic Acid, 82 Prehnitene, 37 iro-Propyl alcohol, 88 -Propyl benzene, 113 1-Propylene Glycol, 84 mo-Propyl Lactate, 88 Pseudodurene, 37 Pykomellitic Acid, go Pyrrole, IT3 Pyruvic acid, 114... 

Piperonylic acid has been made by the oxidation of piperic acid,1 piperonal,1 safrole2 and isosafrole2 with potassium permanganate. It has also been prepared by the action of methylene iodide on protocatechuic acid 3 in the presence of alkali. 

Schalk, M., Cabello-Hurtado, F., Pierrel, M.A., Atanossova, R., Saindrenan, P. and Werck-Reichhart, D. (1998) Piperonylic acid, a selective, mechanism-based inactivator of the trans-annarrate 4-hydroxylase a new tool to control the flux of metabolites in the phenylpropanoid pathway. Plant Physiology, 118 (1), 209-218. 

Piperonylic acid [94-53-1] M 166.1, m 229°. Crystd from EtOH or water. 

Piperonylic acid 1,3-Benzodioxole-5-carboxylic acid Tartronic acid Propanedioic acid, hydroxy-... 

Pipcric acid is insoluble in water, but soluble in aqueous NaOH and aqueous NaHC03. Titration gives an equivalent weight of 215 6. It reacts readily with Br2/CCl4, without evolution of HBr, to yield a compound of formula Ci2Hio04Br4. Careful oxidation of piperic acid yields piperonylic acid, C8H6O4, and tartaric acid, HOOCCHOHCHOHCOOH. 

When piperonylic acid is heated with aqueous HCl at 200° it yields formaldehyde and protocatechuic acid, 3,4-dHiydroxybenzoic acid. 

If chromic acid be used as the oxidizing agent, piperonal and piperonylic acid, melting at 228°, are formed. 

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