1,2-Dichlorobenzene → p-Toluenesulfonic acid

Participants

Reaction Steps

The product, 2-((4-(methylthio)-m-tolyloxy)methyl)-2-imidazoline, was prepared by heating 19.3 g of 4-methylthio-m-tolyloxyacetonitrile, 23.3 g of ethylenediamine p-toluenesulfonate and 75 ml of 1,2-dichlorobenzene substantially as described in previous examples. Upon cooling the reaction mixture, diluting with CH2Cl2 and filtering, 32.5 g of p-toluenesulfonate salt was obtained. The p-toluenesulfonate salt was then slurried in water and CH2Cl2 and then basified. The CH2Cl2 layer was separated and the aqueous layer extracted with chloroform. The extracts were combined, treated with diatomaceous earth and activated charcoal and then filtered. The filtrate was taken to dryness, which gave 13.5 g of the product, 2-((4-(methylthio)-m-tolyloxy)methyl)-2-imidazoline as a white solid, m.p. 102°-104° C.

Provenance & Evidence