In a
2-l. three-necked flask fitted with
stirrer,
dropping funnel, and
thermometer are placed
700 ml. of formic acid (88%) and
140 ml. of hydrogen peroxide (30%, 1.37 moles). While the temperature is kept at 35–40° (Note
1),
116.2 g. (117.3 ml., 1.00 mole) of indene (98%) (Note
2) is added dropwise, with stirring, over a period of 2 hours. An additional
100 ml. of formic acid is used to rinse the last of the
indene from the dropping funnel into the reaction flask. The reaction solution is stirred at room temperature for 7 hours to ensure complete reaction (Note
3). The solution is transferred to a
2- or 3-l. Claisen flask, and the
formic acid is removed under aspirator pressure (b.p.
35–40°/20–30 mm.), care being taken to maintain the boiler temperature below 60° (Note
4). The residue, after being cooled to room temperature, is a yellowish brown crystalline solid (Note
5), the color being due to contamination by a small amount of brownish oil.
In a
5-l. flask fitted with a
long condenser (about 40 cm.) connected to an ice-cooled receiver is placed
2 l. of 7% (by volume) sulfuric acid. The solution is heated to boiling, and the crude
monoformate of
1,2-indanediol is added. Steam is introduced and the mixture is steam distilled, while external heat is applied with a flame in order to maintain the boiler contents at a constant volume of 2 l. The steam distillation is carried out at the rate of about 1 l. per hour until 5–6 l. of distillate have been collected and the
2-indanone has stopped distilling (Note
6). The dark-brown oily residue becomes semisolid at room temperature.
The cold distillate is filtered with suction, and the white crystalline solid is sucked thoroughly dry on the filter (Note
7). The crystals are dried further in a
vacuum desiccator (at about 1 mm.) at room temperature or below for about 12 hours. The melting point of the
2-indanone is
57–58° (Note
8). The yield is
90–107 g. (
69–81%).