Water → Dilauryl Ether

Participants

Reaction Steps

Dimethyl 2,5-dihydroxyterephthalate (5.00 g), bromododecane (11.6 g) and anhydrous potassium carbonate (7.63 g) were reacted in N,N′-dimethylformamide at 120° C. under nitrogen for six hours. The solution was cooled and poured into water. After filtration and washing, 11.0 g of the di-dodecyl ether was obtained. This was hydrolyzed with sodium hydroxide to the diacid salt, acidified and the diacid chloride formed by reaction of 6.6 g of the diacid with a 100% molar excess of thionyl chloride. The acid chloride was added over 30 minutes to a solution of glycidol (2.0 g) and triethylamine (2.56 g) in dry toluene maintained at −10° C. Reaction was continued for 5 hours at 20° C. after which the reaction mixture was extracted with dichloromethane and water and the dichloromethane layer dried over sodium sulfate, filtered and the solvent removed under vacuum. The resulting solid was recrystallized from ethyl acetate to give 2.4 g of a pale yellow solid melting at 66-68° C., the diglycidyl ester of 2,5-didodecyloxyterephthalic acid.

Provenance & Evidence