1-Tetralone

Chemical Properties

Clear amber to brown oily liquid

Uses

1-Tetralone is a reagent used in the synthesis of amino-pyrazolopyridines with anti-NF-κB and pro-apoptotic potential.

Production Methods

Intramolecular acylation of 4-phenylbutyric acid to 1,2,3,4-tetrahydronaphthalen-1-one (1-Tetralone).

Synthesis Reference(s)

Tetrahedron Letters, 32, p. 4291, 1991 DOI: 10.1016/S0040-4039(00)92151-8

Purification Methods

Check the IR first. Purify α-tetralone by dissolving 20mL in Et2O (200mL), washing with H2O (100mL), 5% aqueous NaOH (100mL), H2O (100mL), 3% aqueous AcOH (100mL), 5% NaHCO3 (100mL) then H2O (100mL) and dry the ethereal layer over MgSO4. Filter, evaporate and fractionate the residue through a 6in Vigreux column (p 11) under reduced pressure to give a colourless oil (~17g) with b 90-91o/0.50.7mm. [Snyder & Werber Org Synth Coll Vol III 798 1955.] It has also been fractionated through a 0.5metre packed column with a heated jacket under reflux using a partial take-off head. It has max 247.5 and 290nm (hexane). The phenylhydrazone has m 83o. The 2,4,6-trinitrophenylhydrazone has m 247.5-248o (from EtOH). [Olson & Bader Org Synth Coll Vol IV 898 1963, Beilstein 7 H 370, 7 III 1416, 7 IV 1015.]