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Properties of substance:

α-chlorobenzyl methyl sulfide

Group of substances:

organic

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

C8H9ClS

Structural formula as text:

C6H5CHClSCH3

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. 576 [doi: 10.1021/ja01608a016]

A solution of 34.9 g. (0.20 mole) of benzyl methyl sulfoxide in 40 ml. of methylene chloride was added during 2 hours to a heated solution of 27 g. (0.23 mole) of thionyl chloride in 40 ml. of methylene chloride. The solution was refluxed for an additional hour and distilled giving 25.9 g. (75%) of chloromethyl p-chlorophenyl sulfide, b.p. 109—111° (8 mm.).

Synthesis 2:

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]

A solution of 15.6 g. (0.20 mole) of methyl sulfoxide and 27.6 g. (0.20 mole) of benzyl methyl sulfide in 50 ml. of methylene chloride was added to a heated solution of 26.4 g. (0.22 mole) of thionyl chloride in 40 ml. of methylene chloride during 90 minutes. The mixture was distilled, first at atmospheric pressure to yield 8.0 g. (41%) of chloromethyl methyl sulfide, b.p. 104—106°, and then under vacuum giving 12 g. (35%) of ?-chlorobenzyl methyl sulfide, b.p. 125—130° (15 mm.).

Methyl benzyl sulfide when treated alone with thionyl chloride in the above manner gave no sharp boiling product.

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    © Collected Ruslan Anatolievich Kiper, burewestnik@mail.ru