1-Tetralone

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1-Tetralone[1]
Structural formula of 1-tetralone
Ball-and-stick model of the 1-tetralone molecule
Names
IUPAC name
3,4-Dihydro-2H-naphthalen-1-one
Other names
α-Tetralone; 1-Tetralone
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.692
Properties
C10H10O
Molar mass 146.19 g·mol−1
Density 1.099 g/mL
Melting point 2 to 7 °C (36 to 45 °F; 275 to 280 K)
Boiling point 113 to 116 (6 mmHg)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

1-Tetralone is an organic chemical compound with the molecular formula C10H10O. It is a common intermediate in organic synthesis, it is a ketone derivative of tetralin, a hydrogenated derivative of naphthalene. A related compound is 2-tetralone.

Preparation[edit]

1-Tetralone can be prepared by several methods. A typical methods involve intramolecular cyclisation of phenylbutyric acid.[2]

The Haworth reaction is a classic method for the synthesis of tetralone.[3][4] Benzene is reacted with succinic anhydride by a Friedel–Crafts acylation, the intermediate product is reduced and a second Friedel–Crafts acylation takes place upon the addition of acid.

Haworth reaction

Use[edit]

1-Tetralone is a precursor to 1-naphthol by dehydrogenation:[5]

C10H10O → C10H7OH + H2

References[edit]

  1. ^ α-Tetralone at Sigma-Aldrich
  2. ^ Cecil E. Olson, Alfred R. Bader, and G. Dana Johnson "α-Tetralone" Org. Synth. 1955, 35, 95. doi:10.15227/orgsyn.035.0095
  3. ^ Robert Downs Haworth (1932). "Syntheses of alkylphenanthrenes. Part I. 1-, 2-, 3-, and 4-Methylphenanthrenes". J. Chem. Soc.: 1125. doi:10.1039/JR9320001125. 
  4. ^ Name Reactions: A Collection of Detailed Reaction Mechanisms By Jie Jack Li Published 2003 Springer ISBN 3-540-40203-9
  5. ^ Gerald Booth "Naphthalene Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a17_009.