Acetanisole

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
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.560 Edit this at Wikidata
UNII
  • InChI=1S/C9H10O2/c1-7(10)8-3-5-9(11-2)6-4-8/h3-6H,1-2H3
  • CC(=O)C1=CC=C(C=C1)OC
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).
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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

  1. ^ 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.
  2. ^ Para-Acetanisole, The Good Scents Company
  3. ^ a b 4'-Methoxyacetophenone from PubChem
  4. ^ a b Acetanisole at Sigma-Aldrich
  5. ^ 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.
  6. ^ 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.

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