Novel access to carbonyl and acetylated compounds: the role of the tetra-n-butylammonium bromide/sodium nitrite catalyst was written by Sheykhan, Mehdi;Moafi, Hadi Fallah;Abbasnia, Masoumeh. And the article was included in RSC Advances in 2016.Electric Literature of C8H9NO3 This article mentions the following:
A novel aerobic oxidation of alcs. ArCH(OH)R (Ar = C6H5, 2-O2N-3-CH3-C6H3, 2-carbaldehydefuran-5-yl, etc.; R = H, CH3) without the use of any oxidants was developed. An equimolar catalytic mixture of tetra-n-butylammonium bromide and sodium nitrite catalyzes the aerobic selective oxidation of benzylic alcs. under oxidant-free, base-free and metal-free conditions. The mild reaction conditions allow oxidation of a wide range of benzylic alcs., chemo-selectively to their carbonyl compounds ArC(O)R (68-93% isolated yields). More importantly, high selectivity among different kinds of alcs. (aromatic vs. aliphatic alcs., primary vs. secondary alcs. as well as alcs. having neutral rings vs. electron-deficient rings) is available by this approach. The method surprisingly switched over to be an efficient acetylation approach in the case of aliphatic alcs. without the use of any transition metal, phosphorus or other toxic reagents or any need for using toxic acyl halides, sulfonyl halides, anhydrides, etc. by the use of only acetic acid as a reagent. In the experiment, the researchers used many compounds, for example, (3-Methyl-2-nitrophenyl)methanol (cas: 80866-76-8Electric Literature of C8H9NO3).
(3-Methyl-2-nitrophenyl)methanol (cas: 80866-76-8) belongs to alcohols. Alcohols are weak acids. The most acidic simple alcohols (methanol and ethanol) are about as acidic as water, and most other alcohols are somewhat less acidic. The most common reactions of alcohols can be classified as oxidation, dehydration, substitution, esterification, and reactions of alkoxides.Electric Literature of C8H9NO3
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts