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Properties of substance:

dibenzyl sulfoxide

Group of substances:

organic

Physical appearance:

leaflets crystals

Empirical formula (Hill's system for organic substances):

C14H14OS

Structural formula as text:

C6H5CH2SOCH2C6H5

Melting point (°C):

134

Decomposition temperature (°C):

210

Solubility (g/100 g of solvent):

diethyl ether: soluble [Ref.]
ethanol: soluble [Ref.]
water: soluble (hot) [Ref.]

Synthesis 1:

Reference: Bordwell, F. G., Pitt, B. M. The Formation of α-Chloro Sulfides from Sulfides and from Sulfoxides / Journal of the American Chemical Society. - 1955. - Vol. 77, No. 3 pp. 577 [doi: 10.1021/ja01608a016]

During 16 hours’ reflux of 2.14 g. (0.01 mole) of benzyl sulfide and 4.16 g. (0.04 mole) of thiacyclopentane 1-oxide in 25 ml. of acetic acid containing 5 drops of sulfuric acid a black tarry mixture was formed. The mixture was diluted with water and extracted with 200 ml. of ether and the ether layer was washed three times with 100 ml. of water and then diluted with alcohol. After removal of the ether (steam-bath) and treatment with charcoal, concentration of the solution under reduced pressure gave 0.40 g. (17%) of benzyl sulfoxide, m.p. 131—133°. The m.p. after crystallization from benzene-hexane was 133—134° and was not depressed by an authentic sample.

References:

  1. Dictionary of organic compounds. - vol.1, Abietic acid - Dypnone. - London, 1946. - pp. 672

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    © Collected Ruslan Anatolievich Kiper, burewestnik@mail.ru