Synthesis of tetralin hydroperoxide

Preparation of tetralin hydroperoxide

Preparation of tetralin hydroperoxide

Preparation of tetralin hydroperoxide

A three-necked flask with stirrer, reflux condenser, gas-inlet tube with attached sintered plate, safety wash-bottle is charged with 1 mole of tetraline, 350 ml of 2% sodium carbonate, 1 g of an emulsifier (sodium palmitate or sodium stearate), and 10 ml of an at least 15% solution of the tetralin hydroperoxide (if tetralin hydroperoxide is not available the reaction could be initiated with 0.5 g of azo-bis-isobutyronitrile) are heated on the water bath to the reaction temperature (70-75°C) and a powerful stream of oxygen is passed in until the hydroperoxide content of the solution increases no further (24-48 hours).

Determination of the hydroperoxide content
About 2 ml of the reaction solution is treated with 2 g of sodium chloride, and the organic phase is allowed to separate. 0.4 to 1 g of this is weighed accurately into a 200-ml Erlenmeyer flask with a ground-in stopper. 10 ml of acetic anhydride and 1 to 2 g of potassium iodide are added and, after 10 min, 70 ml of water. Then the mixture is shaken vigorously for 30 sec. The iodine liberated is titrated with 0.1 N sodium thiosulphate solution with starch as indicator.

% hydroperoxide = consumption of Na2S203 (ml) x molecular wt. of tetralin hydroperoxide (164.20 g/mol)/weight of sample (g) x 200

The determination of the hydroperoxide is carried out hourly and the result is plotted on a graph (ordinates: moles of oxygen absorbed; abscissae: time in hours).

Organicum. Practical Handbook of Organic Chemistry, by Heinz Becker, Werner Berger and Günter Domschke, Addison-Wesley Pub. Co, 177-178, (1973)

IUPAC Name

1-hydroperoxy-1,2,3,4-tetrahydronaphthalene

InChI

InChI=1S/C10H12O2/c11-12-10-7-3-5-8-4-1-2-6-9(8)10/h1-2,4,6,10-11H,3,5,7H2

InChI Key

YWBMNCRJFZGXJY-UHFFFAOYSA-N

Canonical SMILES

C1CC(C2=CC=CC=C2C1)OO

Depositor-Supplied Synonyms

Tetralin hydroperoxide, 1,2,3,4-Tetrahydro-1-hydroperoxynaphthalene, Tetralinhydroperoxid [German], Tetralinehydroperoxyde [Dutch], 26447-24-5, 1,2,3,4-tetrahydro-1-naphthalenyl hydroperoxide, Hydroperoxide, 1,2,3,4-tetrahydro-1-naphthyl-, Hydroperoxide, 1,2,3,4-tetrahydro-1-naphthalenyl, Hydroperoxyde de tetraline [French], EINECS 212-230-0, Idroperossido di tetralina [Italian], AI3-12032, 1-hydroperoxy-1,2,3,4-tetrahydronaphthalene, 1,2,3,4-Tetrahydro-1-naphthyl hydroperoxide, 771-29-9, Tetralinhydroperoxid, Tetralinehydroperoxyde, AC1L2CUB, AC1Q7DKF, AC1Q7DKM, Hydroperoxyde de tetraline, Idroperossido di tetralina, Tetralin-1-yl hydroperoxide, SCHEMBL298463, CCRIS 8475, SCHEMBL11577284, KST-1B8740, AR-1B5143, AKOS006276229, LS-77277, OR042438, OR190786, OR250313, FT-0652824, 1-(dioxidanyl)-1,2,3,4-tetrahydronaphthalene, 1-hydroperoxy-1,2,3,4-tetrahydro-naphthalene, A818446, S14-1312

Removed Synonyms

CID69866, 81531-57-9

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