Everything about Oxalyl Chloride totally explained
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Oxalyl chloride is a
chemical compound with the
formula (COCl)
2. This colourless liquid, the di
acid chloride of
oxalic acid, is a useful reagent in
organic synthesis. It can be prepared by treating
oxalic acid with
phosphorus pentachloride.
Applications in organic synthesis
Synthesis of acid chlorides
It is mainly used in
organic synthesis for the preparation of acid chlorides from the corresponding
carboxylic acids. Like
thionyl chloride, the reagent produces volatile side products in this application:
» RCO
2H + (COCl)
2 → RC(O)Cl + HCl +
CO +
CO2
Oxalyl chloride tends to be a milder, more selective
reagent.
Formylation of arenes
Oxalyl chloride reacts with
aromatic compounds in the presence of
aluminium chloride to give the corresponding
acid chloride in a process known as a
Friedel-Crafts acylation. The resulting acid chloride can be hydrolysed in water to form the corresponding
carboxylic acid.
Preparation of diesters
Like other acid chlorides, oxalyl chloride reacts with alcohols to give esters:
» 2 RCH
2OH + (COCl)
2 → RCH
2OC(O)C(O)OCH
2R + 2 HCl
Typically such reactions are conducted in the presence of a base such as
pyridine. The diester derived from
phenol,
phenyl oxalate ester, is Cyalume, the active ingredient in
glow sticks.
Oxidation of alcohols
The combination of
DMSO and oxalyl chloride converts alcohols to the corresponding
aldehydes and
ketones via the process known as the
Swern oxidation.
Precautions
As with all
acyl chlorides, oxalyl chloride reacts with
water liberating
HCl gas. Overall, its effects are comparable to those of
phosgene.
In March 2000 a
Malaysia Airlines Airbus A330 was damaged beyond repair after a falsely declared cargo of oxalyl chloride leaked into the cargo bay.
Further Information
Get more info on 'Oxalyl Chloride'.
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