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Properties of substance:

4-methoxyphenyl methyl sulfide

Group of substances:

organic

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

C8H10OS

Structural formula as text:

CH3SC6H4OCH3

Melting point (°C):

25-26

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. 575 [doi: 10.1021/ja01608a016]


CH3OC6H4Br + Mg → CH3OC6H4MgBr
CH3OC6H4MgBr + (CH3S)2 → CH3OC6H4SCH3 + CH3SMgBr

A solution of 66 g. (0.7 mole) of methyl disulfide in 200 ml. of ether was added slowly to the Grignard reagent prepared from 187 g. (1 mole) of p-bromoanisole and 32 g. (1.5 moles) of magnesium in 500 ml. of ether, giving rise to a moderately exothermic reaction and the appearance of a yellow precipitate. After standing overnight a solution of 180 ml. of concentrated hydrochloric acid in 300 ml. of water was added slowly to the mixture (methyl mercaptan liberated). The ether extract was separated and dried over anhydrous sodium sulfate. Distillation gave 101 g. (93% based on methyl disulfide) of p-methoxyphenyl methyl sulfide, b.p. 98—100° (4 mm.).

Vapour pressure (Torr):

4 (99°C)

References:

  1. Dictionary of organic compounds. - Vol. 3, naphthacarbazole - zygadenine. - Ì.: ÈÈË, 1949. - pp. 753

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    © Collected Ruslan Anatolievich Kiper, burewestnik@mail.ru