Acetanisole
| Names | |
|---|---|
| Preferred IUPAC name
1-(4-Methoxyphenyl)ethan-1-one | |
| Other names
4-Acetylanisole; para-Acetanisole; 4-Methoxyacetophenone; Linarodin; Novatone; Vananote; Castoreum anisole; 4-Methoxyphenyl methyl ketone
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.002.560 |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C9H10O2 | |
| Molar mass | 150.177 g·mol−1 |
| Appearance | White solid[1] |
| Density | 1.094 g/cm3 |
| Melting point | 38.2 °C (100.8 °F; 311.3 K)[3] |
| Boiling point | 254 °C (489 °F; 527 K)[3] |
| 2470 mg/L[2] | |
| Hazards | |
| Flash point | 138 °C (280 °F)[4] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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Acetanisole is an organic compound with the formula CH3OC6H4C(O)CH3. It can be viewed as derivative of acetophenone and of anisole. It has an aroma described as sweet, fruity, nutty, and similar to vanilla. In addition the odor of acetanisole is sometimes described as butter-like or caramel-like.[4] It is used commercially in some soap fragrances. It is a component of anise oil.[1]
Preparation
Acetanisole can be prepared synthetically by Friedel-Crafts acylation of anisole with acetyl chloride:[1]
Reactions
4-Methoxyacetophenone is a standard substrate or product of much research, such as transfer hydrogenation[5] and directed arylations.[6]
References
- ^ a b c Panten, Johannes; Surburg, Horst (2016). "Flavors and Fragrances, 3. Aromatic and Heterocyclic Compounds". Ullmann's Encyclopedia of Industrial Chemistry. pp. 1–45. doi:10.1002/14356007.t11_t02. ISBN 978-3-527-30673-2.
- ^ Para-Acetanisole, The Good Scents Company
- ^ a b 4'-Methoxyacetophenone from PubChem
- ^ a b Acetanisole at Sigma-Aldrich
- ^ 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. Bibcode:1997JAChS.11911108P. doi:10.1021/ja972593s.