Hexanoyl chloride, 2-(2,4-bis(1,1-dimethylpropyl)phenoxy)- → HCID 18763750, compound

Participants

Reaction Conditions

Reaction Steps

In a 500-ml flask, place 17.4 g (0.04 m) of 3-N-benzyl-5-(-t-butylphenoxy)-6-nitro-benzoxazol-2-one (5b), 70 ml of isopropyl alcohol and 35 ml of toluene. Heat the mixture to 60° C. Add 0.8 g of 5% Pd/C wet with 1 ml of water and 16.8 g (0.2 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 6-amino-5-(4-t-butylphenoxy)-benzoxazol-2-one (6b; Y=4-t-butylphenoxy) to 15° C. and add 16.2 g (0.04 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 60 ml of toluene slowly in drop wise over 1 hr period. Stir the mixture at 15° C. for another 30 min. Filter off catalyst and wash with a small volume of toluene and water. Separate toluene solution, wash with 100 ml of 1N HCl twice, and concentrate under a reduced pressure to a thick oil. Add 180 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 18.1 g (72%) of 6-{2-(2,4-di-t-pentylphenoxy)hexanoyl}amino-5-(4-t-butylphenoxy)-benzoxazol-2-one (Formula I, Y=4-t-butylphenoxy and R′=1-(2,4-di-t-pentylphenoxy)pentyl).

Provenance & Evidence