Hexanoyl chloride, 2-[2,4-bis(1,1-dimethylpropyl)phenoxy]- → HCID 13007985, compound

Participants

Reaction Conditions

Reaction Steps

In a 500-ml flask, place 18.9 g (0.05 m) of 5-benzyloxy-2-(4-t-butyl-phenoxy)-nitrobenzene (3a), 80 ml of isopropyl alcohol and 40 ml of toluene. Heat the mixture to 60° C. Add 1.0 g of 5% Pd/C wet with 1 ml of water and 21.0 g (0.25 m) of potassium formate in 30 ml of water. Stir the reaction mixture vigorously at 60°-70° C. for 3 hrs under nitrogen. Cool the reaction mixture containing 5-amino-4-(4-t-butylphenoxy)phenol (4a, Y=4-t-butylphenoxy) to 15° C. and add 20.3 g (0.05 m×1.05 @95%) of 2-(2,4-di-t-pentylphenoxy)hexanoyl chloride (R′COZ; R′=1-(2,4-di-t-pentylphenoxy)pentyl and Z=Cl) in 80 ml of toluene slowly over 10 min. Stir the mixture at room temperature for another 30 min and add 100 ml of water. Filter off catalyst and wash with a small volume of toluene and water. Separate toluene solution, wash with 200 ml of 1N HCl twice, and concentrate under a reduced pressure to a thick oil. Add 200 ml of heptane to the oil with gentle stirring. Cool in an ice-water bath for 1 hr. Collect solid, wash with heptane, and dry in a vacuum oven to give 27.0 g (92%) of 4-(4-t-butylphenoxy)-5-{2-(2,4-di-t-pentylphenoxy)hexanoyl}amino-phenol (5a; Y=4-t-butylphenoxy and R′=1-(2,4-di-t-pentylphenoxy)pentyl).

Provenance & Evidence