A mixture of
150 g. (0.82 mole) of benzophenone (Note
1), one drop of glacial
acetic acid (Note
2), and
665 g. (850 cc., 11 moles) of isopropyl alcohol (Note
3) in a
1-l. round-bottomed flask is warmed to 45°. The flask is closed with a
tight cork firmly wired or tied in place, and is supported in an inverted position in a
tripod and exposed to direct sunlight. After three to five hours of bright sunshine crystals of
benzopinacol begin to appear; after eight or ten days of exposure, depending upon the intensity of the light (Note
4), the flask is filled with crystals of
benzopinacol. The solution is chilled in ice and the crystalline product is filtered with suction, washed with a small quantity of
isopropyl alcohol, and allowed to dry in the air. The filtrate is reserved for subsequent reductions (see below). The yield of practically pure
benzopinacol, m.p.
188–190° (Note
5), is
141–142 g. (
93–94 per cent of the theoretical amount). The product is sufficiently pure for most purposes. It may be crystallized by dissolving it in
1 l. of hot benzene, filtering, and adding
400 cc. of hot ligroin (b.p.
90–100°) to the hot filtrate. After cooling in ice and filtering there is obtained
129–130 g. of purified product. The melting point is not changed by this purification.
To the
isopropyl alcohol filtrate is added another
150-g. portion of benzophenone, and the solution is exposed to sunlight as in the first reduction. The
benzopinacol which separates is filtered and dried. The yield in the second and subsequent runs is
142–143 g. (
94–95 per cent of the calculated amount). This procedure can be repeated with the same filtrate until six or seven portions
(900–1050 g.) of benzophenone have been reduced.