4-Methylacetophenone

4-Methylacetophenone

Identifiers
CAS Number	122-00-9
ECHA InfoCard	100.004.105
CompTox Dashboard (EPA)	DTXSID9044374
Properties
Chemical formula	C9H10
Molar mass	118.179 g·mol−1
Appearance	white or colorless oil
Density	1.006 g/cm3
Melting point	28 °C (82 °F; 301 K)
Boiling point	224 °C (435 °F; 497 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

4-Methylacetophenone is an organic compound with the formula CH₃C₆H₄C(O)CH₃. It is related to acetophenone with a methyl group at the 4-position. Two isomers, 2-methylacetophenone and 3-methylacetophenone, are also known. It is a fragrance of commercial significance. ^[1]

Synthesis and reactions

It is prepared by acetylation of toluene. ^[2]

Oxidation with hot nitric acid followed bt potassium permanganate gives terephthalic acid. ^[3] It undergoes most of the reactions of acetophenone: reduction to the alcohol followed by dehydration gives 4-methylstyrene.

Occurrence

4-Methylacetophenone occurs naturally in some woods.

References

1. 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. Röper, Michael; Gehrer, Eugen; Narbeshuber, Thomas; Siegel, Wolfgang (2000). "Acylation and Alkylation". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a01_185. ISBN   978-3-527-30385-4.
3. C. F. Koelsch (1946). "Terephthalic Acid". Organic Syntheses. 26: 95. doi:10.15227/orgsyn.026.0095.