Benzopolymethylene compounds. IV. The two ar-aldehydes of tetralin was written by Braun, Julius V.;Moldaenke, K.;Dirlam, H.;Gruber, H.. And the article was included in Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen in 1922.HPLC of Formula: 29809-13-0 This article mentions the following:
When tetralin (A) is treated with CO and HCl in the presence of AlCl3 it is impossible to prevent the greater part of the A from condensing with itself in the same way as it does with AlCl3 alone (Schroeter, C. A. 15, 525); the small part that does react with the CO and HCl gives exclusively the ar-tetralin-β-aldehyde (B) (2 g. from 100 g. A). Both B and the α-isomer (C) can be obtained from the ar-tetralin-β- and α-methylamines (D and E, resp.) through the corresponding alcs. Bamberger and Lodter’s statement that α-C10H7CH2NH2 on reduction takes up the H in the substituted nucleus (Ber. 20, 1708(1887)) seemed to exclude this compound and the β-isomer as the starting points in the synthesis of B and C. Accordingly the NH2 group in the α- and β-tetralylamines was replaced by CN, which was then reduced to CH2NH2, but the yields are poor. On repeating B.’s work, however, it was found that it is the unsubstituted nucleus which takes up the H on reduction and that the pure D and E can easily be obtained in this way. ar-α-Tetralyl cyanide, obtained in 22% yield from the amine by the Sandmeyer reaction, b15 153°, solidifies to a yellowish crystalline mass m. 48° (Bamberger and Bordt, Ber. 22, 625(1889), describe it as an oil b121 277-9°, which does not solidify), hydrolyzed by fuming HCl in a sealed tube at 120° to the acid, m. 150° (B. and H. give 123°); reduction of the nitrile with Na and alc. gives chiefly A and only about 1/3 is converted into E, oil of basic odor, b11 149-52°, eagerly absorbs CO2 from the air, also obtained in almost 90% yield from α-C10H7CH2NH2 with 8 atoms of Na in AmOH (in EtOH there is very little reaction); hydrochloride, silvery needles from alc., m. 253°; picrate, golden yellow prisms from alc., m. 242°; acetyl derivative, m. 125°; benzoyl derivative, m. 144°; phenylurea, m. 199°; phenylthiourea, m. 153°. The corresponding ar-α-tetralylmethylamine (from α-C10H7CN with Na and alc.) forms a hydrochloride m. 230°, picrate m. 169-70°, phenylurea m. 126°, and benzoyl derivative m. 125°. ar-β-Tetralyl cyanide (obtained in 45-60% yield), liquid of a not unpleasant odor, b11 151-2°, m. 20-1°, gives with Na and EtOH 30% of D, b11 146-8°; hydrochloride, m. 248°; picrate, m. 215°; benzoyl derivative, long needles from alc., m. 165°, b10 260-5°; p-nitrobenzoyl derivative, m. 170°; phenylthiourea, m. 130°. D is also obtained in almost 90% yield from β-C10H7CH2NH2 with Na and AmOH. ar-α-Tetralylcarbinol, obtained in 80% yield from E diazotized in AcOH with the calculated amount of NaNO2 and heated on the H2O bath until the evolution of gas ceases, b12 154-5°, gives in H2SO4 with the calculated amount of K2Cr2O7 1/3 of its weight of C, b12 131-3°, as an almost odorless oil; semicarbazone, m. 187°. KMnO4 smoothly oxidizes C to the acid. ar-β-Tetralylcarbinol (yield, 70%), faintly yellow liquid with a strong pleasant odor, b14 148-52°, gives on oxidation 25% of B, liquid of characteristic peppermint-like odor, b14 138°; semicarbazone, m. 219°. In the experiment, the researchers used many compounds, for example, 5,6,7,8-Tetrahydronaphthalene-1-carbonitrile (cas: 29809-13-0HPLC of Formula: 29809-13-0).
5,6,7,8-Tetrahydronaphthalene-1-carbonitrile (cas: 29809-13-0) belongs to nitriles. The electronic structure of nitriles is very similar to that of an alkyne with the main difference being the presence of a set of lone pair electrons on the nitrogen. In conventional organic reductions, nitrile is reduced by treatment with lithium aluminium hydride to the amine. Reduction to the imine followed by hydrolysis to the aldehyde takes place in the Stephen aldehyde synthesis, which uses stannous chloride in acid.HPLC of Formula: 29809-13-0
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts