Sodium Chloride → HCID 18600187, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 0.933 g. of 3-O-n-hexadecyl-L-ascorbic acid in 7.5 ml. of anhydrous DMF was added slowly at ambient temperature under a nitrogen atmosphere to a suspension of 2.45 millimoles of NaH in 10 ml. of anhydrous DMF in a 50 ml., 3-neck round-bottom flask equipped with magnetic stirrer, drying tube and dropping funnel. The reaction mixture was stirred for 25 minutes (until H2 evolution stopped) at which time the sodium salt (on the 2-hydroxy) of 3-O-n-hexadecyl-L-ascorbic acid had formed. A solution of 0.295 g. of benzyl chloride in 2 ml. of anhydrous DMF was added. The reaction mixture was stirred at ambient temperature for about 50 minutes. The reaction temperature was then raised to 90° C., at which temperature stirring was continued for an additional 50 minutes. The reaction mixture was cooled and saturated aqueous sodium chloride (brine) added. The resulting aqueous mixture was extracted with ethyl acetate. The ethyl acetate extract was washed with brine and dried. The dried extract was decolorized with charcoal, filtered and the volatile constituents removed in vacuo. The resulting yellow syrup was chromatographed over silica gel 60 using 1:9 ethyl acetate-toluene as the eluant. Fractions shown by TLC to contain the desired product were combined and the solvent removed therefrom. 694 mg. (62% yield) of a yellow waxy solid comprising purified 2-O-benzyl-3-O-n-hexadecyl-L-ascorbic acid were obtained.

Provenance & Evidence