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