Hydrochloric Acid → HCID 19862973, compound

Participants

Reaction Steps

To the above 1-carbobenzoxymethyl-1-carbomethoxyethylcyclohexane (40.4g) in dioxane (300ml) was added 1N NaOH (150 ml) dropwise over 2 hours with stirring at room temperature. After 6 hours the reaction was neutralized with 1N HCl then the dioxane was evaporated. The cloudy solution was diluted with water, acidified with 1N HCl, then extracted two times with ethyl acetate, washed with saturated NaCl (agueous), dried with MgSO4, filtered and then concentrated to an oil. By 1H-NMR no mono-methyl ester could be seen in the crude reaction mixture, the major by-product being the di-acid. The product was purified by flash chromatography (silica gel, eluted with CHCl3, MeOH,HOAc 99:1:0.1) then distilled free of the residual benzyl alcohol to give 1-carbobenzoxymethyl-1-carboxyethylcyclohexane. (29.6 g, 76%) 1H-NMR (CDCl3) δ7.05(s,5H); 4.9(s,2H); 2.35-2.1(m,2H); 2.2(s,2H); 1.85-1.55(m,2H); 1.35(br s,10H)

Provenance & Evidence