Phenol → HCID 85443899, compound

Participants

Reaction Steps

A mixture consisting of 14.2 g. (0.068 mole) phosphorus pentachloride, 100 ml. carbon tetrachloride, and 16.78 g. (0.065 mole) p-(methylthio)benzoic acid 2-phenylhydrazide (prepared in Part A above) was reacted at 25°C. until evolution of gas ceased. The reaction mixture was then heated to the reflux temperature and a clear solution resulted. The solution was chilled in ice and a suspension of 20.7 g. (0.22 mole) phenol in 50 ml. carbon tetrachloride was added. After removing the carbon tetrachloride by evaporation on a rotary evaporator at 31°C. the resulting suspension of product in triphenylphosphate was filtered. The filter cake was washed with technical hexane ((Skellysolve B, a mixture of isomeric hexanes having a boiling range between 146° and 156° Fahrenheit), and then was washed with diethyl ether. Crystallization from 75 ml. ethyl acetate gave 8.10 g. (44.9% yield) of p-(methylthio)-benzoyl chloride phenylhydrazone having a melting point of 138.5° to 142.5°C. Recrystallization from a mixture of ethyl acetate and the Skellysolve B gave the compound with the same melting point.

Provenance & Evidence