Acetanisole

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Acetanisole
Acetanisole V.1.svg
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 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
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
AppearanceWhite solid [1]
Density 1.094 g/cm3
Melting point 38.2 °C (100.8 °F; 311.3 K) [2]
Boiling point 254 °C (489 °F; 527 K) [2]
2470 mg/L [3]
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]

Contents

Preparation

Acetanisole can be prepared synthetically by Friedel-Crafts acylation of anisole with acetyl chloride: [1]

Acetanisol Synthesis.svg

Reactions

4-Methoxyacetophenone is a standard substrate or product of much research, such as transfer hydrogenation [5] and directed arylations. [6]

References

  1. 1 2 3 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. 1 2 4'-Methoxyacetophenone from PubChem
  3. ↑ Para-Acetanisole, The Good Scents Company
  4. 1 2 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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