Toluene → HCID 13008312, compound

Participants

Reaction Conditions

Reaction Steps

In a 500-ml flask, place 32.0 g (0.15 m×1.3) of 4-t-pentylphenol, 250 ml of toluene, 15 ml of N,N-dimethylacetamide, and 1 1.22 g (0.15 m×1.2@90%) of KOH flakes. Heat the mixture under reflux with Dean-Stark trap to collect approximately 5 ml of water and 20 ml of toluene over 1 hr. Cool white slurry mixture to 90° C., and add 41.8 g (0.15 m) of 2-benzyloxy-5-chloro-4-nitroaniline (2) and 1 g of tetrabutylammonium bromide. Heat under reflux for 1 hr. Addition of 1 g of phase transfer agent, tetrabutylammonium bromide, and heat under reflux for 1 hr period is repeated 3 more times. At the end of the 4 hrs reflux period, cool the reaction mixture to 90° C., add 100 ml of hot water and stir for a few min. Separate toluene solution, wash with 100 ml of hot water, concentrate the reaction mixture by distilling off toluene under a reduced pressure at a pot temperature of 60° C. Add 200 ml of heptane slowly at 60° C., cool to room temperature, and let it stand over night. Collect solid, wash with 10% toluene in heptane, dry in air to give 55.5 g (91%) of 2-benzyloxy-5-(4-t-pentylphenoxy)-4-nitro-aniline (3b; Y=4-t-pentylphenoxy).

Provenance & Evidence