ORGLIST: Re: Reduction of an alcohol with HI-acid

Date view Thread view Subject view Author view Attachment view

From: by way of Joao Aires de Sousa (alihoyer$##$
Date: Mon May 19 1997 - 11:08:51 EDT

> I heard of a certain reduction with hydriodic acid (57%) and red
> phosphorus wich reduced a secondary amino-alcohol (HO-group on the alpha
> position) to the corresponding carbohydrate. It was a one pot method (I
> think it went directly thrugh the halogenated state to the end product) in
> quite good yields.
> They mentioned that since HI can be generated by dripping cleaned red
> phosphorus in H2O to Iodine Crystalls suspendet in H2O, the whole reduction
> could also be made by reacting Jodine Crystalls and red phosphorus in water
> together with the alcohol to be reduced.

Diphenylcarbinols are reduced by hydriodic acid. This reaction may be
performed in the presence of phosphite, like triethyl phosphite,
which reduces the iodine formed bach to iodide.

Have you checked to see whether Fieser & Fieser, or your local
equivalent entitled something like "Everything about All Reagents in
Organic Chemistry", describes the use of hydriodic acid for reduction
of alcohols?

ORGLIST - Organic Chemistry Mailing List
WWW Homepage and Archive:
List coordinator: Joao Aires de Sousa (jas$##$

Date view Thread view Subject view Author view Attachment view

This archive was generated by hypermail 2.1.4 : Fri Sep 19 2003 - 12:14:31 EDT