Uses
Doebner-Miller reaction the 4- nitrocinnamaldehyde and 2-methylaniline in concentrated HC1 give the corresponding 8-methyl-2-phenylquinoline (3: R = 4'-N02) directly. The asymmetric Friedel-Crafts-type alkylation in aqueous media reaction of 4-Nitrocinnamaldehydr with N-methyl indole using trifluoroacetic acid (TFA) salt of the PEG-PS-supported prolyl peptide having the polyleucine tether as a catalyst. 4-Nitrocinnamaldehyde has been used in the preparation of 2, 2-[(E)-3-(4-nitrophenyl) prop-2-ene-1,1-diyl] bis(3-hydroxy-5, 5-dimethylcyclohex-2-en-1-one).
Synthesis
5.0 g (66 mmol) of p-nitrobenzaldehyde and 10.0 mL of acetaldehyde were added to a three-necked flask, and to a dropping funnel was added
10 mL of 30% mass fraction potassium hydroxide-methanol solution with magnetic stirring, and the reaction flask was cooled with an ice-salt bath, and when the temperature was reduced to 0-5C, 5 mL of potassium hydroxide-methanol solution was added slowly and dropwise with magnetic stirring, and the reaction was carried out for 40 min, and then 5 mL of potassium hydroxide-methano was added dropwise.
Alcohol solution, continue the reaction for 40min at about 10C, cool the reaction mixture below 5C to solidify, add 16mL of acetic anhydride and
Heated on a water bath for 30min, poured into 120mL of hot water, added 16mL of concentrated hydrochloric acid, heated on a water bath for 20min, and left to stand for 24h. Dialyzed crystals, pumped, washed, and recrystallized in aqueous acetic acid with a mass fraction of 30% to obtain 1.6g of yellow crystals, which is 4-nitrocinnamaldehyde, and the calculated product yield was 45.3%.
