To a mixture of 292 g. (332 cc., 3.7 moles) of dry benzene
and 116 g. (73.2 cc., 0.75 mole) of dry carbon tetrachloride (Note 1)
, in a 1-l. flask
provided with a reflux condenser
having a calcium chloride tube
at its upper end, is added 100 g. (0.75 mole) of anhydrous aluminum chloride
in lumps (Note 2)
. The flask is at once immersed in ice water to within 5 cm. of the top, and allowed to stand for twenty-four hours, the temperature of the water being allowed to rise to that of the room (Note 3)
. One hundred and ten grams (153 cc., 1.48 moles) of anhydrous ether
is added in small portions, through the condenser, the flask being shaken occasionally during the twenty minutes required for the addition.
The mixture is allowed to stand for twenty-four hours, and is then poured into a 5-l. flask
containing 650 g. of ice and 25 cc. of concentrated hydrochloric acid
. One liter of benzene
is then added, and the mixture heated on a steam bath
under a return condenser
. After gently boiling for five or ten minutes, the mixture is allowed to cool to 40–50°, when the benzene
layer is separated, washed with 700 cc. of warm water containing 25 cc. of concentrated hydrochloric acid
, and distilled. After the benzene
has been removed under atmospheric pressure, the residue is transferred to a 300-cc. flask
and distilled under reduced pressure, and a fraction boiling over the range 190–215°/10 mm.
collected (Note 4)
. This weighs 135–160 g.
; it solidifies on cooling. It is recrystallized from 550–650 cc. of ethyl alcohol (Note 5)
, and a colorless product, crystallizing in needles which melt sharply at 92°
, is obtained. This is filtered off and washed twice with 30-cc. portions of fresh alcohol
. The alcoholic mother liquor is concentrated and the residue distilled under reduced pressure, material which distils over at 190–200°/10 mm.
being collected. This is recrystallized from ethyl alcohol
, and 6–7 g.
more of pure material is thus obtained. The total yield of recrystallized product is 125–154 g.
per cent of the theoretical amount).