Sodium Hydroxide → HCID 15015792, compound

Participants

Reaction Steps

Finally, phenacyl 3-benzyloxy-2-n-tetradecyl-octadecanoate (V) (1.81 g, 2.57 millimole) was dissolved in a mixed solvent (70 ml) of tetrahydrofuran and methanol (1:1) and 1N sodium hydroxide (7.70 ml, 7.70 millimole) was added thereto, and the mixture was reacted at 65° C. for 2.5 hours. The solvent was distilled off from the reaction mixture, and water and tetrahydrofuran were added to dissolve the residue. Then the solution was acidified with 2N hydrochloric acid (to pH of about 2) with ice cooling, and extracted with ethyl acetate, and the organic phase was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off from the organic phase, the residue was dissolved in a developing solvent (n-hexane:ethyl acetate=8:2), and the obtained solution was purified over a silicagel column (n-hexane:ethyl acetate=8:2). The fast eluting fractions comprising impurities were discarded and the later colorless fractions were pooled. The solvent was evaporated off from the pooled fractions, and the residue was purified over a silicagel column (benzene:ethyl acetate=9:1) again, to give 3-benzyloxy-2-n-tetradecyl-octadecanoic acid (VI) (878 mg, yield 58%) in the form of colorless oil.

Provenance & Evidence