Hydrogen Peroxide → 4-(Phenethyl)benzoyl chloride

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Reaction Conditions

Reaction Steps

This peroxide was synthesized from the corresponding acid chloride and sodium peroxide. First, 4-bibenzylcarboxylic acid chloride was prepared from 4-bibenzylcarboxylic acid and thionyl chloride (see the synthesis of 2-bibenzylcarboxylic acid chloride above). The acid chloride was purified by vacuum distillation (bp=104-106° C./120-130, μHg), and solidified upon cooling. The synthesis of the peroxide was performed with NaOH/H2O2 and the acid chloride in tetrahydrofuran. Here, 12.0 ml 30% H2O2 was added to 4.8 g NaOH in 30.0 ml H2O and the solution cooled to 5° C. A solution of 2.0 g 4-(phenethyl)benzoyl chloride in 2.0 ml tetrahydrofuran was then added and the reaction mixture stirred for one hour. The crude peroxide was filtered off and recrystallized from chloroform/methanol, mp=145° C. (decomp.). The yield was 41%. The peroxide proved to be quite insoluble in common solvents, except for chloroform and large amounts of benzene. NMR δ(ppm): 2.9-3.0 (m, 8, —CH2—CH2—), 7.1-7.3, 7.9-8.0 (m, m, 18, aromatic H).

Provenance & Evidence