4-Nitrobenzaldehyde → 1-methyl-4-[(1E)-2-(4-nitrophenyl)ethenesulfonyl]benzene

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To 15 g (85.47 mmol) of methyl p-tolyl sulfone dissolved in 450 cm3 of tetrahydrofuran are added, at a temperature in the region of 0° C. under an argon atmosphere, 117.5 cm3 (188 mmol) of a 1.06 M solution of n-butyl-lithium in hexane. After stirring for 30 minutes at a temperature in the region of 0° C. are added, under an argon atmosphere, 13 cm3 (85.47 mmol) of diethylchlorophosphate dissolved in 70 cm3 of tetrahydrofuran. After stirring for 30 minutes at a temperature in the region of 0° C., the reaction mixture is cooled to a temperature in the region of −78° C., followed by addition, under an argon atmosphere, of 13.05 g (85.47 mmol) of 4-nitrobenzaldehyde dissolved in 130 cm3 of tetrahydrofuran. After stirring for 1 hour at a temperature in the region of −78° C., the temperature of the reaction mixture is allowed to rise to a temperature in the region of 20° C., 100 cm3 of water are added and the mixture is concentrated under reduced pressure (2.7 kPa) to give a beige-coloured solid. The solid is stirred in 250 cm3 of water for 20 minutes, filtered, washed with three times 40 cm3 of water and oven-dried under reduced pressure (2.7 kPa) at 35° C. for 5 hours to give 25.43 g of 1-[(E)-2-(4-methylphenyl)sulfonylvinyl]-4-nitrobenzene in the form of a beige-coloured solid melting at 176° C.; M.W.=303, IE: m/z=303 M+, m/z=239 [M-SO2]+, m/z=139 [CH3-Ph-SO]+.

Herkunft & Nachweise