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Synlett 2007(16): 2607-2608  
DOI: 10.1055/s-2007-986658
SPOTLIGHT
© Georg Thieme Verlag Stuttgart · New York

Sodium Hypochlorite (NaOCl)

Hojat Veisi*
Faculty of Chemistry, Bu-Ali Sina University, Hamadan 6517838683, Iran
e-Mail: h_organo2005@yahoo.com;
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Publication History

Publication Date:
12 September 2007 (online)

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Introduction

Sodium hypochlorite (NaOCl), commonly known as bleach, is a strong oxidizing and bleaching agent. This reagent is one of the most important oxidants in organic synthesis and is a source of oxygen for olefin epoxidation. [1] NaOCl has found wide application in organic synthesis, such as chlorination of benzene derivatives, [2] epoxidation of olefines without metal catalysts, [3] enantioselective epoxidation of alkenes with catalyst, [4] selective oxidation of benzylic hydrocarbons, [5] oxidation of alcohols, [6] synthesis of 3-oxazolins, [7] dihydroxylation of olefins, [8] oxidation of aliphatic ethers to esters under ruthenium catalysis, [9] etc. NaOCl has also been found useful for H2S-odor control via oxidation of H2S (Scheme 1).

Scheme 1

Commercially, NaOCl is available in solutions of various concentrations, with 12.5% (w/w) being the most common for bulk usage. This product contains 0.15 kg of available chlorine per liter. [10] It is a liquid (ρ = 1.206 g/ml at 25 °C) which boils at 111 °C

Sodium hypochlorite is a solution made from the reaction of chlorine with a sodium hydroxide solution (Scheme 2).

Scheme 2

NaOCl is corrosive and oxidising, it has a variety of uses, and is an excellent disinfectant/antimicrobial agent. The advantages of using NaOCl include operational simplicity, availability, selectivity, and low cost, and it is a green medium for organic reactions.