# Acetanisole

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> Markdown URL: https://mediated.wiki/source/Acetanisole.md
> Source: https://en.wikipedia.org/wiki/Acetanisole
> Source revision: 1327680821
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{chembox
| Watchedfields = changed
| verifiedrevid = 477238683
| ImageFile = Acetanisole V.1.svg
| ImageSize = 200px
| PIN = 1-(4-Methoxyphenyl)ethan-1-one
| OtherNames = 4-Acetylanisole; ''para''-Acetanisole; 4-Methoxyacetophenone; Linarodin; Novatone; Vananote; Castoreum anisole; 4-Methoxyphenyl methyl ketone
| Section1 = {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 7196
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 0IRH2BR587
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 100-06-1
|   PubChem = 7476
|   SMILES = CC(=O)C1=CC=C(C=C1)OC
|   InChI = 1S/C9H10O2/c1-7(10)8-3-5-9(11-2)6-4-8/h3-6H,1-2H3
  }}
| Section2 = {{Chembox Properties
|   C=9|H=10|O=2
|   Appearance = White solid<ref name=Ullmann/>
|   Density = 1.094 g/cm<sup>3</sup>
|   MeltingPtC = 38.2
|    MeltingPt_ref = <ref name=Pubchem>{{PubChem|7476|4'-Methoxyacetophenone}}</ref>
|   BoilingPtC = 254
|    BoilingPt_ref = <ref name=Pubchem/>
|   Solubility = 2470 mg/L<ref name=goodscents>[https://www.thegoodscentscompany.com/data/rw1000111.html Para-Acetanisole], The Good Scents Company</ref>
  }}
| Section3 = {{Chembox Hazards
|   MainHazards =
|   FlashPt = {{convert|138|C|F}}<ref name=Aldrich>[https://www.sigmaaldrich.com/US/en/product/aldrich/w200506 Acetanisole] at [Sigma-Aldrich](/source/Sigma-Aldrich)</ref>
|   AutoignitionPt =
  }}
}}

'''Acetanisole''' is an [organic compound](/source/organic_compound) with the formula {{chem2|CH3OC6H4C(O)CH3}}.  It can be viewed as derivative of [acetophenone](/source/acetophenone) and of [anisole](/source/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.<ref name=Aldrich/> It is used commercially in some soap fragrances.  It is a component of [anise oil](/source/anise_oil).<ref name=Ullmann>{{cite book |last1=Panten |first1=Johannes |last2=Surburg |first2=Horst |title=Ullmann's Encyclopedia of Industrial Chemistry |chapter=Flavors and Fragrances, 3. Aromatic and Heterocyclic Compounds |date=2016 |pages=1–45 |doi=10.1002/14356007.t11_t02 |isbn=978-3-527-30673-2 }}</ref>

==Preparation==
Acetanisole can be prepared [synthetically](/source/organic_synthesis) by [Friedel-Crafts acylation](/source/Friedel-Crafts_acylation) of anisole with [acetyl chloride](/source/acetyl_chloride):<ref name=Ullmann/>
:500px

==Reactions==
4-Methoxyacetophenone is a standard substrate or product of much research, such as [transfer hydrogenation](/source/transfer_hydrogenation)<ref>{{cite journal |doi=10.1021/jo010721w |title=Metal−Ligand Bifunctional Catalysis: A Nonclassical Mechanism for Asymmetric Hydrogen Transfer between Alcohols and Carbonyl Compounds |date=2001 |last1=Noyori |first1=Ryoji |last2=Yamakawa |first2=Masashi |last3=Hashiguchi |first3=Shohei |journal=The Journal of Organic Chemistry |volume=66 |issue=24 |pages=7931–7944 |pmid=11722188 }}</ref> and directed arylations.<ref>{{cite journal |doi=10.1021/ja972593s |title=Palladium-Catalyzed α-Arylation of Ketones |date=1997 |last1=Palucki |first1=Michael |last2=Buchwald |first2=Stephen L. |journal=Journal of the American Chemical Society |volume=119 |issue=45 |pages=11108–11109 |bibcode=1997JAChS.11911108P }}</ref>

== References ==
{{reflist}}

Category:Food additives
Category:Piceol ethers
Category:Sweet-smelling chemicals

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Adapted from the Wikipedia article [Acetanisole](https://en.wikipedia.org/wiki/Acetanisole) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Acetanisole?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.