Preparation of phenyl sodium
A mixture of 150 ml. of toluene, 11.5 g. (0.5 gram atom) of sodium sand, and 22.5 g. (0.2 mole) of chlorobenzene is stirred at room tem¬perature under an atmosphere of dry nitrogen. After about 45 minutes an exothermic reaction sets in, and the temperature of the reaction mixture is held below 40° with a cooling bath. The entire reaction requires about 2 hours. The toluene solution of phenylsodium should be used immediately. The yield of organometallic compound is 87%. The yield is determined from the amount of benzoic acid obtained after pouring the above solution on excess crushed solid carbon dioxide followed by acidification.
Reference: J. Am. Chem. Soc, 62, 1517 (1940).