Benzoyl chloride, also known as benzenecarbonyl chloride, is an organochlorine compound with the formula . It is a colourless, fuming liquid with an irritating odour, and consists of a benzene ring () with an acyl chloride () substituent. It is mainly useful for the production of organic peroxide but is generally useful in other such as in the preparation of , , , and .[
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Preparation
Benzoyl chloride is produced from benzotrichloride using either water or benzoic acid:[
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As with other , it can be generated from the parent acid and standard chlorinating agents such as phosphorus pentachloride, thionyl chloride, and oxalyl chloride. It was first prepared by treatment of benzaldehyde with chlorine.
An early method for production of benzoyl chloride involved chlorination of benzyl alcohol.[ US1851832, 29 March 1932]
Reactions
It reacts with water to produce hydrochloric acid and benzoic acid:
Benzoyl chloride is a typical acyl chloride. It reacts with alcohols to give the corresponding . Similarly, it reacts with Amine to give the amide.[Prasenjit Saha, Md Ashif Ali, and Tharmalingam Punniyamurthy "Ligand-free Copper(ii) Oxide Nanoparticles Catalyzed Synthesis Of Substituted Benzoxazoles" Org. Synth. 2011, volume 88, pp. 398. . (an illustrative reaction of an amine with benzoyl chloride).]
It undergoes the Friedel-Crafts acylation with aromatic compounds to give the corresponding and related derivatives.
Benzoyl peroxide, a common reagent in polymer chemistry, is produced industrially by treating benzoyl chloride with hydrogen peroxide and sodium hydroxide:
Modified benzoyl chlorides
Many substituted derivatives of benzoyl chloride are known. 4-Nitrobenzoyl chloride is a precursor to the anesthetic procaine.[ One example is 4-chlorobenzoyl chloride, a precursor to 4-chloro-4'-hydroxybenzophenone, which is used to make high performance .]
Safety
Benzoyl chloride is toxic and a serious skin irritant.
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