Side chain hydroxylation of aromatic compounds by fungi. 1. Products and stereochemistry was written by Holland, Herbert L.;Bergen, Eleanor J.;Chenchaiah, P. Chinna;Khan, Shaheer H.;Munoz, Benito;Ninniss, Ronald W.;Richards, Denise. And the article was included in Canadian Journal of Chemistry in 1987.Synthetic Route of C9H9NO This article mentions the following:
The fungus Mortierella isabellina can convert ethylbenzene and a number of para-substituted derivatives to the corresponding optically active 1-phenylethanols with enantiomeric excesses between 5% and 40% and chem. yields up to 45%. 2-Ethylnaphthalene, 2-ethylthiophene, and n-propylbenzene were similarly converted, as were the bicyclic compounds indane and tetralin. In most cases, the R absolute configuration of product predominated. The fungi Cunninghamella echinulata elegans and Helminthosporium species are also capable of performing some of these transformations. M. isabellina And C. elegans also produce 2-phenylethanols as products in some cases. The highest enantiomeric excesses during benzylic hydroxylation were obtained with Helminthosporium and are attributable, at least in part, to further stereoselective oxidation of the alchol. Cross-induction experiments with M. isabellina indicate that the same enzyme may be responsible for the benzylic hydroxylation of ethylbenzene, 2-ethylthiophene, and 2-ethylnaphthalene. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Synthetic Route of C9H9NO).
(R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.Synthetic Route of C9H9NO
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts