2-Acetylfuran

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2-Acetylfuran
Names
Preferred IUPAC name
1-(Furan-2-yl)ethan-1-one
Other names
1-(Furan-2-yl)ethanone
1-(2-Furanyl)-ethanone
2-Acetylfuran
Acetyl furan
2-Furyl methyl ketone
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.013.416 Edit this at Wikidata
UNII
  • InChI=1S/C6H6O2/c1-5(7)6-3-2-4-8-6/h2-4H,1H3
    Key: IEMMBWWQXVXBEU-UHFFFAOYSA-N
  • InChI=1/C6H6O2/c1-5(7)6-3-2-4-8-6/h2-4H,1H3
    Key: IEMMBWWQXVXBEU-UHFFFAOYAG
  • CC(=O)C1=CC=CO1
Properties
C6H6O2
Molar mass 110.112 g·mol−1
Appearance Low melting solid
Density 1.0975 at 20 °C
Melting point 30 °C (86 °F; 303 K)
Boiling point 168 to 169 °C (334 to 336 °F; 441 to 442 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

2-Acetylfuran has a low melting point and a high boiling point.[1][2] The solid melts at 30 °C and has a density of 1.0975 g/ml at 20 °C, while the normal boiling point of the liquid is 168–169 °C.[3] 2-Acetylfuran is a useful intermediate in the synthesis of fine chemicals and pharmaceuticals, and is used in the production of the generic cephalophosphorin antibiotic cefuroxime.[4]

Synthesis[edit]

2-Acetylfuran was prepared by Ashina in 1914 via the reaction of the methyl Grignard reagent on 2-furonitrile.[3] Modern industrial synthesis generally involves the Friedel–Crafts acylation of furan with acetic anhydride.

Applications[edit]

Pharmaceuticals[edit]

A one-pot synthesis of an intermediate to the HIV integrase inhibitor S-1360 was based on the Friedel-Crafts alkylation of 2-acetylfuran with 4-fluorobenzyl chloride using zinc chloride catalyst.[5]

Reaction of 2-acetylfuran with aqueous sodium nitrite gave 2-furanyloxoacetic acid, an intermediate to Cefuroxime, a second-generation cephalosporin antibiotic.[6]

Artificial flavouring[edit]

This compound has a balsamic, caramellic, sweet, almond, nutty profile with recommended uses in bakery, chocolate, cocoa, coffee, nut and tomato products.[7]

See also[edit]

References[edit]

  1. ^ Howard D. Hartough; Kosak, Alvin I. (1948). "Acylation of thiophene and furan by means of boron trifluoride. VII". Journal of the American Chemical Society. 70 (2): 867. doi:10.1021/ja01182a510.
  2. ^ Walther Borsche; Leditschke, Heinrich; Lange, Karl (1938). "Cleavage of the furan ring by primary aromatic amines and hydrochloric acid". Berichte der Deutschen Chemischen Gesellschaft B. 71: 957–66.
  3. ^ a b Asahina, Y.; Murayama, Y. (1914). "Ethereal oil of Elsholtzia cristata Willdenow (Lablatae)". Archiv der Pharmazie. 252: 435–48. doi:10.1002/ardp.19142520609. S2CID 94708979.
  4. ^ Rong-geng Wang; Liu, Cheng-ping; Zhu, Kun-peng; Du, Hai-lin; Liu, Lie-yi (2004). "Side chain of cefuroxime: (Z)-2-methoxyimino-2-(fury-2-yl)acetic acid ammonium salt". Jingxi Yu Zhuanyong Huaxuepin. 12 (17): 10–11.
  5. ^ Kenji Izumi; Kabaki, Mikio; Uenaka, Masaaki; Shimizu, Sumio (2007). "One-Step Synthesis of 5-(4-Fluorobenzyl)-2-furyl Methyl Ketone: A Key Intermediate of HIV-Integrase Inhibitor S-1360". Organic Process Research & Development. 11 (6): 1059–1061. doi:10.1021/op700117q.
  6. ^ Rui-min Lv; Zhang, Zhi-de; Zhang, Zhi-cheng (2005). "The research for the synthesis of 2-methoxyimino-2-furylacetic acid". Shandong Huagong. 34 (6): 5–8.
  7. ^ "Online Compendium".
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