Tetralin Tetralone

Catalyst Temp (°C) tetralin tetralone tetralol others3... 

A further example is given below illustrating the use of a dibasic anhydride (succinic anhydride) the succinoylation reaction is a valuable one since it leads to aroyl carboxylic acids and ultimately to polynuclear hydrocarbons. This general scheme of synthesis of substituted hydrocarbons through the use of succinic anhydride is sometimes called the Haworth reaction. Thus a-tetralone (see below) may be reduced by the Clemmensen method to tetralin (tetrahydronaphthalene) and the latter converted into naphthalene either catal3d.ically or by means of sulphur or selenium (compare Section, VI,33). 

The most important process to produce 1-naphthalenol was developed by Union Carbide and subsequently sold to Rhc ne-Poulenc. It is the oxidation of tetralin, l,2,3,4-tetrahydronaphthalene/719-64-2] in the presence of a transition-metal catalyst, presumably to l-tetralol—1-tetralone by way of the 1-hydroperoxide, and dehydrogenation of the intermediate ie, l-tetralol to 1-tetralone and aromatization of 1-tetralone to 1-naphthalenol, using a noble-metal catalyst (58). 1-Naphthol production in the Western world is around 15 x 10 t/yr, with the United States as the largest producer (52). 

A three-necked round-bottom flask is fitted with a dropping funnel, a thermometer, and a magnetic stirrer and is heated in a water bath to 30°. Tetralin (1.32 g, 0.01 mole) and 50 ml of 3.5 Anitric acid solution are placed in the flask and brought to temperature. Ceric ammonium nitrate (21.9 g, 0.04 mole) is dissolved in 100 ml of 3.5 N nitric acid, and the solution is added dropwise to the reaction mixture at a rate such that the temperature does not rise and only a pale yellow color is evident in the reaction mixture. At the completion of the reaction (1 to 2 hours), the mixture should be colorless. The solution is cooled to room temperature, diluted with an equal volume of water, and extracted twice with ether. The ether solution is dried with anhydrous sodium sulfate, filtered, and the ether is evaporated. The residue may be distilled to yield a-tetralone (bp 113-11676 mm or 170749 mm) or may be converted directly to the oxime, which is recrystallized from methanol, mp 88-89°. 

Autoxidation may in some cases be of preparative use thus reference has already been made to the large-scale production of phenol+ acetone by the acid-catalysed rearrangement of the hydroperoxide from 2-phenylpropane (cumene, p. 128). Another example involves the hydroperoxide (94) obtained by the air oxidation at 70° of tetrahydro-naphthalene (tetralin) the action of base then yields the ketone (a-tetralone, 95), and reductive fission of the 0—0 linkage the alcohol (a-tetralol, 96) ... 

The conversion of tetralin to a-tetralone may be achieved under aqueous biphasic conditions in the presence of 02, using NiCl2 as a catalyst, as shown in Scheme 9.3 [7], It is necessary to use tetraethylene pentamine (TEPA) as a surface-active ligand, as well as an emulsifier, dodecyl sodium sulfate. Some alcohol and naphthol by-products were also observed, and a radical chain mechanism has been proposed for this reaction. 

An alternative procedure for the isolation of a-tetralone, which involves removal of the excess tetralin from the peroxide by vacuum distillation and subsequent treatment of the peroxide with alkali, is not recommended since heating of the peroxide may cause a violent explosion. 

For qualitative analyses, the GC system was equipped with a J W Scientific HP-5 or a Supelco Simplicity 1 fused-silica capillary column. Injector and detector temperatures were set at 220 °C and 240 °C respectively the oven temperature was programmed from 60 to 230 °C at 40 °C min V Helium was employed as carrier gas (1 mL min ). Compound identification was based on a comparison of mass spectra with those of synthetic racemic and enantiomeric-enriched samples. The retention times for tetralin, 1-tetralol and 1-tetralone were 5.6 min, 6.5 min and 6.6 min respectively. 

Tetralone from tetralone, alpha-naphthol, tetralin NaY Methyl acetate [241]... 

RuC1 (CH3CN)3 is made from RuCl with and CH CN it is brick-red. The X-ray crystal structure of RuCljCCHjCbOj.dCHjCN shows a mer-octahedral geometry. The electrochemistry of the complex was stucUed as were IR and mass spectra. As RuCljCCHjCbOj/aq. L CIO )/ electrodes it oxidised tetralin to tetralone [786].. ... 

Tetrachloroethane, purification of, 176 Tetradecanoic acid, 938, 940, 941 n-Tetradecyl bromide, 283 1 2 3 4-Tetrahydrocarbazole, 852 Tetrahydrofuran, 271 Tetrahydrofurfuryl chloride, 896, 901 Tetrahydropyran, 271 Tetralin, dehydrogenation of, 948, 949 purification of, 949 a-Tetralone, 728, 737 Tetramethyl base, 987 pp -Tetramethyldiaminodiphenyl-methane, 987... 

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