To a mixture of
120 g. (118.5 ml., 1 mole) of acetophenone (Note
1),
123 g. (109 ml., 1 mole) of ethyl chloroacetate, and
200 ml. of dry benzene in a
1-l. three-necked round-bottomed flask, fitted with a stirrer and low-temperature thermometer, is added, over a period of 2 hours,
47.2 g. (1.2 moles) of finely pulverized sodium amide. The temperature is kept at 15–20° by external cooling (Note
2). After the addition has been completed, the mixture is stirred for 2 hours at room temperature, and the reddish mixture is poured upon 700 g. of cracked ice, with hand stirring. The organic layer is separated and the aqueous layer extracted once with
200 ml. of benzene. The combined
benzene solutions are washed with three 300-ml. portions of water, the last one containing
10 ml. of acetic acid. The
benzene solution is dried over
25 g. of anhydrous sodium sulfate, filtered, the drying agent rinsed with a little dry
benzene, and, after removal of the solvent, the residue is fractionated under reduced pressure, using a
modified Claisen flask. The fraction boiling at
107–113°/3 mm. is collected separately and used for the preparation of
hydratropaldehyde (p. 733). Redistillation yields a product which boils at
111–114°/3 mm. (Note
3). The yield is
128–132 g. (
62–64%) (Note
4).