To 500 cc. of absolute alcohol (Note 1) in a 1-l. flask fitted with a reflux condenser is added gradually 46 g. (2 atoms) of sodium in thin slices (Note 2) at such a rate that the mixture boils steadily. When all the sodium has been added, the mixture is heated on the steam bath until the few remaining pieces of sodium barely react. Pure commercial molten phenol is now added gradually through the condenser until all the sodium has reacted, and then the remainder of 188 g. (2 moles) of phenol is added. This is followed by the addition of 221 g. (2 moles) of redistilled glycerol α-monochlorohydrin (p. 294) in small portions, the rather vigorous reaction being allowed to complete itself before each subsequent addition.

When all has been added, the mixture is heated on the steam bath for about one hour. The end of the reaction is determined by withdrawing a sample, filtering it, and heating the filtrate in which little or no precipitate should form. The mixture is filtered hot by suction through filter cloth or heavy filter paper (Note 3), the precipitate being washed with three 50-cc. portions of absolute alcohol. The filtrate and washings are distilled on the steam bath under slightly reduced pressure until no more alcohol comes over; the residue, which sets to a white waxy solid on cooling, is transferred to a distilling flask and distilled under reduced pressure, the fraction boiling at 175–190°/15 mm. being collected. In this way 235–275 g. of a product melting at 43–49° is obtained. On redistillation, 205–215 g. (61–64 per cent of the theoretical amount) of a fraction which boils at 185–187°/15 mm. and melts at 48–53° is obtained (Note 4).