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).