Gu, Yuanyun;Zhang, Zhen;Wang, Yan-En;Dai, Ziteng;Yuan, Yaqi;Xiong, Dan;Li, Jie;Walsh, Patrick J.;Mao, Jianyou published 《Benzylic Aroylation of Toluenes Mediated by a LiN(SiMe3)2/Cs+ System》 in 2022. The article was appeared in 《Journal of Organic Chemistry》. They have made some progress in their research.Reference of Methyl 3-methylbenzoate The article mentions the following:
Chemoselective deprotonative functionalization of benzylic C-H bonds is challenging, because the arene ring contains multiple aromatic C(sp2)-H bonds, which can be competitively deprotonated and lead to selectivity issues. Recently it was found that bimetallic [MN(SiMe3)2 M = Li, Na]/Cs+ combinations exhibit excellent benzylic selectivity. Herein, is reported the first deprotonative addition of toluenes to Weinreb amides mediated by LiN(SiMe3)2/CsF for the synthesis of a diverse array of 2-arylacetophenones. Surprisingly, simple Me benzoates also react with toluenes under similar conditions to form 2-arylacetophenones without double addition to give tertiary alc. products. This finding greatly increases the practicality and impact of this chem. Some challenging substrates with respect to benzylic deprotonations, such as fluoro and methoxy substituted toluenes, are selectively transformed to 2-aryl acetophenones. The value of benzylic deprotonation of 3-fluorotoluene is demonstrated by the synthesis of a key intermediate in the preparation of Polmacoxib.Methyl 3-methylbenzoate (cas: 99-36-5) were involved in the experimental procedure.
Methyl 3-methylbenzoate (cas: 99-36-5) is a common ester.Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids.Reference of Methyl 3-methylbenzoate Esters are responsible for the aroma of many fruits, including apples, durians, pears, bananas, pineapples, and strawberries.
Reference:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics