1-Tetralone

1-Tetralone^[1]

Names
IUPAC name 3,4-Dihydro-2H-naphthalen-1-one
Other names α-Tetralone; 1-Tetralone
Identifiers
CAS Number	529-34-0
ChemSpider	10273
Jmol interactive 3D	Image
PubChem	10724
InChI InChI=1S/C10H10O/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-2,4,6H,3,5,7H2 Key: XHLHPRDBBAGVEG-UHFFFAOYSA-N InChI=1/C10H10O/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-2,4,6H,3,5,7H2 Key: XHLHPRDBBAGVEG-UHFFFAOYAD
SMILES C1CC2=CC=CC=C2C(=O)C1
Properties
Chemical formula	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

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

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

C₁₀H₁₀O → C₁₀H₇OH + H₂

References

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.