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.[3] 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.[1]
Preparation
Acetanisole can be prepared synthetically by Friedel-Crafts acylation of anisole with acetyl chloride:
Application
It is used as a cigarette additive,[4] a fragrance,[1] and a flavoring in food.[5]
Reactions
4-Methoxyacetophenone is a standard substrate or product of much research, such as transfer hydrogenation[6] and directed arylations.[7]
References
- ^ a b c d Para-Acetanisole, The Good Scents Company
- ^ a b 4'-Methoxyacetophenone from PubChem
- ^ a b Acetanisole at Sigma-Aldrich
- ^ Tobacco Documents | Profiles | Additives | Acetanisole Archived April 11, 2008, at the Wayback Machine
- ^ 21 CFR 172.515
- ^ 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.
- ^ 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.