Synthesis
Add 30g styrene, 30ml dichloromethane, 43.5g trichloromethane, and 1.2g TEBA (benzyltriethylammonium chloride) to a 250ml four-necked flask. Heat to reflux, add alkaline solution (28.5g NaOH + 28.5ml water) dropwise, and reflux for 8 hours. Cool to room temperature, add 60ml water, stir for 10 minutes, allow to stand for separation, extract the aqueous layer with petroleum ether, combine the organic layers, dry with anhydrous sodium sulfate, filter, and distill the filtrate under high vacuum using an oil pump. Slowly heat until the distillate stabilizes, then distill at approximately 95–100℃ to obtain a colorless liquid.
Yield: 88.6%; HPLC purity: 99.2%.
Chemical Properties
clear colorless to very slightly yellow liquid
Uses
(2,2-Dichlorocyclopropyl)benzene may be used in the synthesis of
p-(2,2-dichlorocyclopropyl)aniline.
Synthesis Reference(s)
Organic Syntheses, Coll. Vol. 7, p. 12, 1990
Synthetic Communications, 25, p. 3821, 1995
DOI: 10.1080/00397919508011456Tetrahedron Letters, 16, p. 3013, 1975
