“Oxidizing” actions of alkalies. II. Aromatic hydroxy aldehydes was written by Lock, Gunther. And the article was included in Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen in 1929.HPLC of Formula: 60463-12-9 This article mentions the following:
Like o-HOC6H4CHO, the m-and p-compounds on fusion with KOH decompose almost quantitatively into H2 and KOC6H4C02K, but while the o- and p-compounds begin to evolve H below 110°, the m-compound (I) begins to react only at about 190°, and moreover the yellow color which is produced when the aldehyde is mixed with the powd. KOH gradually disappears without any external heating. The cause of these phenomena is that I undergoes the Cannizzaro reaction with solid KOH or its solution at room temperature and at 190° the KOH further reacts with the m-HOC6H4CH2OH resulting from the disproportionation. The gradual disappearance of the yellow color at room temperature marks the 1st reaction, the yellow phenolate changing into the colorless salts of HOC6H4CO2H and HOC6H4CH20H. The old rule that a phenolic HO group prevents the disproportionation into alc. and acid holds, therefore, only when the HO group is in the o- or p-position to the CHO group. With aqueous KOH I reacts at room temperature without evolution of gas and gives more than 90% of the acid and alc. In parallel experiments with I and KOH on the 1 hand and the alc. and KOH on the other, to determine whether a Cannizzaro reaction precedes the evolution of H, the evolution of H in both cases began at 190°, showing that it is produced from the alc. The 6-Br derivative of I reacts visibly more sluggishly with 50% KOH; the mixt must be slightly warmed but the end result is the same as with I itself. The 4- and 6-NO2 derivatives likewise do not undergo the Cannizzaro reaction as readily as I, giving 38-9 and 70%, resp., of the corresponding alc. The 4-nitro-3-hydroxybenzyl alc. (II) so obtained m. 97° but depresses about 30° the m. p. of the 3,4-isomer, likewise m. 97°, obtained by Stoermer by introducing the CH2OH group into o-O2NC6H4OH. There are conflicting data in the literature as to whether or not p-HOC6H4CHO (III) changes into the alc, and acid with alkalies at room temperature; L. finds that it undergoes no change when allowed to stand 5 weeks, protected from the air in excess of 50% KOH; on fusion it begins to evolve H at about 110° while the alc. does not react below l65° 3,4-(HO)2C4H3CHO (IV) behaves quite like III both on fusion with KOH and with 50% KOH at room temperature Since the p-HO group in IV prevents the Cannizzaro reaction, its 2 Me ethers, vanillin (V) and isovanillin (VI) should, and as a matter of fact do, behave differently. V is unchanged at room temperature but on fusion evolves H at 110° and gives a mixture of 3,4-(HO)2C6H3C02H and about 24% 4,3-HO(MeO)C6H3CO2H after 3 hrs. at 150-210°, while VI is converted into the alc, and acid and does not evolve H below about 190°. 6-Bromo-3-hydroxybenzyl alc. (yield, 70%), m. 142°, has a burning taste and causes sneezing, gives a blue-violet color with aqueous FeCl3, a yellowish color with alkalies, a flocculent precipitate with Br water, does not react with NH3-AgNO3, dissolves in concentrated H2S04 without color. 6-Nitro compound, m. 120.5°, forms a yellow aqueous solution turned intensely yellow by alkalies, gives a red-violet color with FeCl3, forms an intensely S-yellow salt with basic Pb acetate, does not react with NH3-AgN03, dissolves in concentrated H2S04 with yellow color. II is cream-yellow while Stoemer’s compound is green-yellow; otherwise the 2 isomers greatly resemble each other; both form green-yellow aqueous solutions, give no characteristic color with FeCl3, form red-yellow solutions with aqueous alkalies, do not react with NH3-AgN03 even on boiling, form almost colorless precipitates with Br water; with concentrated H2SO4 II forms a deep red solution and with aqueous Pb(OAc)2 yields a cinnabar-red precipitate while the S. compound dissolves in H2S04 with yellow color and forms a reddish yellow Pb salt. Isovanillyl alc. (yield, 80%), m. 132°, gives a green color with FeCl3, dissolves in H2S04 with Bordeaux-red color. In the experiment, the researchers used many compounds, for example, 3-(Hydroxymethyl)-4-nitrophenol (cas: 60463-12-9HPLC of Formula: 60463-12-9).
3-(Hydroxymethyl)-4-nitrophenol (cas: 60463-12-9) belongs to alcohols. Alcohols are among the most common organic compounds. They are used as sweeteners and in making perfumes, are valuable intermediates in the synthesis of other compounds, and are among the most abundantly produced organic chemicals in industry. Secondary alcohols are easily oxidized without breaking carbon-carbon bonds only as far as the ketone stage. No further oxidation is seen except under very stringent conditions.HPLC of Formula: 60463-12-9
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts