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Synlett 2010(18): 2825-2826  
DOI: 10.1055/s-0030-1259002
SPOTLIGHT
© Georg Thieme Verlag Stuttgart ˙ New York

1,3-Dichloroacetone

Vittorio Pace*
Department of Organic and Pharmaceutical Chemistry, Faculty of Pharmacy, Complutense University of Madrid, Pza. Ramón y ­Cajal s/n, 28040 Madrid, Spain
e-Mail: vpace@farm.ucm.es;
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Publication History

Publication Date:
22 October 2010 (online)

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Introduction

1,3-Dichloroacetone (CAS: 534-07-6) is the simplest and most common example of the α,α′-dihaloketone derivatives. It is a crystalline solid (mp 39-41 ˚C), corrosive, toxic, and has to be handled in a fume hood. It shows a good solubility in organic solvents and a very high high chemical reactivity, justified by the presence of three vicinal electrophilic carbons, which enables it to undergo several chemical transformations. Although it is commercially supplied, it may be prepared by chlorination of acetone in methanol as proposed by Gallucci. [¹] Alternatively, an expeditious synthesis has been reported by Barluenga via the in situ formation of a lithium carbenoid, such as chloromethyllithium, which reacts with the ethyl ester of the chloroacetic acid, as shown in Scheme  [¹] . [²]

Scheme 1