P Tolylmercuric chloride

In a 2-1. round-bottom flask fitted with a reflux condenser and an efficient glass stirrer, are placed 700 cc. of 95 per cent ethyl alcohol, 100 g. of recrystallized p-tolylmercuric chloride (p. 99), and 160 g. of sodium iodide (80 per cent excess). This mixture is boiled with vigorous stirring (Note 2) for fifteen hours the solid does not entirely enter into solution at any time. The mixture is then thoroughly cooled and filtered by suction and the solid washed with water until free of inorganic halide. It is then dried in an air-oven at 40° and recrystallized from 500 cc. of boiling xylene (Note 3). In this way 45-50 g. (78-85 per cent of the theoretical amount) of a product melting at 238° is obtained. 

Di-/>-tolylmercury (Coll. Vol. 1, 226) In 93.5 per cent yields by refluxing an alcoholic suspension of p-tolylmercuric chloride with sodium carbonate and hydrazine hydrate. Gilman and Barnett, Rec. trav. chim. 55, 563 (1936). 

Although thienyl compounds of the type RHgX react with potassium iodide in acetone to give the type R Hg, this has only been noted in benzenoid derivatives in the case of p-tolylmercuric chloride, when a large excess of potassium iodide is used. With phenyl and a-naphthyl-mercuric chlorides only the corresponding iodides are produced. The... 

Whitmore and co-workers" prepared p-tolylmercuric chloride by heating an cquimolecular mixture of sodium p-toluenesulfinate and mercuric chloride in boiling water until evolution of sulfur dioxide ceased (2 hrs.). 

Preparation. The synthesis of p-chloromercuribenzoic acid is a simple procedure which requires no special apparatus. The procedure which follows is adapted from that of Whitmore and Woodward (145). The reaction is given in equation (17). 120 g. of NaOH is dissolved in 1.8 liters of distilled water in a 3-liter beaker equipped with a mechanical stirrer. 50 g. of p-tolylmercuric chloride... 

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