RE: ORGLIST: conversion of OH group to SH

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From: Guido de Silvestri (guidods$##$etb.net.co)
Date: Wed May 03 2006 - 12:51:12 EDT

Dear Madhav...

This kind of processes has to be carrying about within two stages:

As a first step, a synthesis of an alkylhalide from the alcohol can be
possible using thionyl chloride:

ROH +SOCL2 = RCl+SO2 +HCl

Here, pyridine is used as an alkaline absorption agent, yielding the HCl
to pyridine chloride

In a second stage, the alkyl halide (that it is easy to separate from
the reaction mixture), could react with a metallic hydrosulfide making a
nucleophylic substitution, into an alcoholic solution:

RCl + NaSH = RSH + NaCl

In addition, this process is very useful to the primaries merchaptans
synthesis, but not when a secondary or a tertiary halide is involved,
because those could be easy deydrogenalized in presence of strong bases.

Best regards,

Guido de Silvestri
Process Engineer

-----Mensaje original-----
De: everybody-bounces$##$orglist.net [mailto:everybody-bounces$##$orglist.net]
En nombre de madhav mallia
Enviado el: Miércoles, 03 de Mayo de 2006 06:16 a.m.
Para: everybody$##$orglist.net
Asunto: ORGLIST: conversion of OH group to SH

i want to convert aliphatic alcohol to thiol. what are
the options available? help needed.

thanks in advance

madhav

                
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