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18th March 2011 @ 03:33
Preparation of p-toluyl chloride from toluyl acid via nucleophilic substitution.

Reaction Scheme


Start time: 12:40pm 18/03/2011
End time: 5:10pm 18/03/2011

Thionyl chloride (sulfurous dichloride, 31.3 mL, 431 mmol, 3 eq., MW=119 g/mol, d=1.638 g/mL) was added to toluyl acid (4-methylbenzoic acid, 19.57 g, 143.7 mmol, MW=136.1 g/mol) and stirred over a heating mantle under reflux conditions for 2 hrs. Side products (hydrochloric acid gas, sulfur dioxide gas) were vented into the fume hood. Product (mp= 95°C/10mmHg) was distilled for 0.5 hrs to collect pure p-tutoyl chloride.

Hazard and Risk Assessment form
HRAF CS1-1-84.pdf


Yield: 20.3g (131.3mmol, 89%) of liquid p-tutoyl chloride.
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