The oxidation of aromatic and aliphatic oxo compounds with nitrobenzene in alkaline media was written by Kratzl, K.;Hoyos, F. E.;Silbernagel, H.. And the article was included in Monatshefte fuer Chemie in 1960.Synthetic Route of C8H8O3 This article mentions the following:
The usual oxidative degradation process in lignin chemistry to vanillin, etc. by PhNO2 (I) was applied to model compounds Oxo compounds were oxidized to dioxo compounds which, under conditions of the benzilic acid rearrangement and eventual Cannizzaro reaction, gave hydroxy acids. Further oxidation gave oxo acids which decarboxylated to aldehydes, i.e., vanillin. PhAc derivatives maintained the C sequence as shown by labeled C atoms. Thus, 5 g. pinacolone (II), 10 g. I, and 80 ml. 2N NaOH at 165° for 3.75 hrs. gave 14% trimethyllactic acid (III). Similarly treated were (compound, temperature, time, % products given): II, 175°, 3 hrs., 49.5% III, 26% (CO2H)2, 0.7% of an oxo acid; cyclohexanone, 100°, 40 min., 7% 1-hydroxycyclopentanecarboxylic acid; benzylacetone, 165°, 3.5 71.8% benzyllactic acid, 4.2% of an oxo acid; phenylacetic acid, 165°, 3.75 hrs., 5.8% benzoylformic acid (IV), 7% BzOH from a second batch; PhAc, 165°, 3 hrs., 67% IV; o-hydroxyacetophenone, 165°, 3.75 hrs., 12-15% salicylic acid, 44% of an oxo acid; acetovanillone (V), 165°, 3.75 hrs., good yield of vanillin (VI); acetoveratrone, 165°, 3.5 hrs., 90% vanilloylformic acid (VII), 4.25% VI, and 0.5% vanillic acid; veratrylactone, 165°, 3.5 hrs., 3.8% veratroylformic acid, 2.5% VI, and veratraldehyde; isoeugenol, 165°, 3.5 hrs., 55% o-vanillin. V with m-O2NC6H4SO3Na gave VII. Isoacetovanillone gave 26% isovanilloylformic acid. In the experiment, the researchers used many compounds, for example, 3-Hydroxy-5-methoxybenzaldehyde (cas: 57179-35-8Synthetic Route of C8H8O3).
3-Hydroxy-5-methoxybenzaldehyde (cas: 57179-35-8) belongs to ethers. Of all the functional groups, ethers are the least reactive ones. Ether bonds are quite stable towards bases, oxidizing agents and reducing agents. But on the other hand, ethers undergo cleavage by reaction with acids. Ethers can form hydrogen bonds with other molecules (alcohols, amines, etc.) that have O―H or N―H bonds. The ability to form hydrogen bonds with other compounds makes ethers particularly good solvents for a wide variety of organic compounds and a surprisingly large number of inorganic compounds.Synthetic Route of C8H8O3
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem