4-Nitrophenol → HCID 14742807, compound

Participants

Reaction Steps

A stirred mixture of (E)-3-(1-butyl-6-methoxy-2-naphthalenyl)-2-propenoic acid (1.5 g) and 4-nitrophenol (0.81 g) in dichloromethane, was cooled in an ice bath, during the addition of a solution of 1,3-dicyclohexyl- carbodiimide (1.1 g) in dichloromethane (5 mL) then the reaction was stirred at room temperature over the weekend. After the precipitated dicyclohexylurea was removed by filtration, the filtrate was concentrated and applied to a column of silica gel (25 g) made up in dichloromethane-hexane (2:1). Elution with the same solvent mixture and concentration of the appropriate fractions yielded 2 g of (E)-3-(1-butyl-6-methoxy-2-naphthalenyl)-2-propenoic acid 4-nitrophenyl ester. Crystallization of the material from 2-propanol gave 1.85 g of the active ester, mp 140°-141° C. Anal. Calcd for C24H23NO5 : C, 71.10; H, 5.72; N, 3.45 Found: C, 70.98; H, 5.50; N, 3.33

Provenance & Evidence