Acetanisole is an aromatic chemical compound with an aroma described as sweet, fruity, nutty, and similar to vanilla. In addition acetanisole can sometimes smell like butter or caramel. Its chemical names are based on considering the structure as either an acetyl (methyl-ketone) analog of anisole. Other names It can also be seen as a methyl ether analog of acetophenone.
Acetanisole is found naturally in castoreum, the glandular secretion of the beaver.
Preparation
Acetanisole can be prepared synthetically by Friedel-Crafts acylation of anisole with acetyl chloride:
Application
It is used as a cigarette additive,3 a fragrance,4 and a flavoring in food.5
Reactions
4-Methoxyacetophenone is a standard substrate or product of much research, such as transfer hydrogenation6 and directed arylations.7
References
Acetanisole at Sigma-Aldrich https://www.sigmaaldrich.com/US/en/product/aldrich/w200506 ↩
Para-Acetanisole, The Good Scents Company http://www.thegoodscentscompany.com/data/rw1000111.html ↩
Tobacco Documents | Profiles | Additives | Acetanisole Archived April 11, 2008, at the Wayback Machine http://tobaccodocuments.org/profiles/additives/acetanisole.html ↩
Para-Acetanisole, The Good Scents Company http://www.thegoodscentscompany.com/data/rw1000111.html ↩
21 CFR 172.515 /wiki/Title_21_of_the_Code_of_Federal_Regulations ↩
Noyori, Ryoji; Yamakawa, Masashi; Hashiguchi, Shohei (2001). "Metal−Ligand Bifunctional Catalysis: A Nonclassical Mechanism for Asymmetric Hydrogen Transfer between Alcohols and Carbonyl Compounds". The Journal of Organic Chemistry. 66 (24): 7931–7944. doi:10.1021/jo010721w. PMID 11722188. /wiki/Doi_(identifier) ↩
Palucki, Michael; Buchwald, Stephen L. (1997). "Palladium-Catalyzed α-Arylation of Ketones". Journal of the American Chemical Society. 119 (45): 11108–11109. doi:10.1021/ja972593s. /wiki/Doi_(identifier) ↩