Bromide ion → N-(4-Formyl-3-methylphenyl)acetamide

Participants

Reaction Steps

In a 500-ml flask, place 12.0 g (0.3 m) of sodium hydroxide pellets, 6.41 g (0.2 m) of sulfur powder, 18.0 g (0.075 m) of sodium sulfide nonahydrate, and 140 ml of distilled water. Heat the mixture with good stirring to about 70 C. to make an orange-red solution. In a 100-ml beaker, place 22.7 g (0.15 m) of 4-nitro-o-xylene, 2.4 g (5 mole %) of tetrabutlammonium bromide and 30 ml of isopropyl alcohol. Warm it to 50 C. with occasional stirring to make a clear pale-yellow solution. Add the solution in the beaker to the mixture in the 500-ml flask and use 10 ml of isopropyl alcohol to rinse the beaker and add to the reaction mixture. Heat the mixture with vigorous stirring under gentle reflux for 4.5 hours. Distill off isopropyl alcohol till approximately 50 ml of distillate is collected and pot/vapor temperature reaches to 100 C. Cool the reaction mixture to 20 C. Add 100 ml of propyl acetate and stir vigorously at room temperature for 5 minutes, and let layers settle. Separate off bottom water layer. Wash propyl acetate solution with 100 ml of water. Add 27 g (0.45 m) of acetyl anhydride slowly to propyl acetate solution containing 4-amino-2-methylbenzaldehyde. Stir the mixture at 40 C. for 1 hour. Add 100 ml of heptane and cool the mixture to room temperature. Stir slurry in a cold water bath for 1 hour. Collect solid, wash with 1:1 propyl acetate/heptane and dry to give 18.0 g (68%) of 4-acetylamino-2-methylbenzaldehyde.

Provenance & Evidence