1-Bromododecane → Diethyl dodecyl(methyl)propanedioate

Participants

Reaction Conditions

Reaction Steps

A solution of 48.72 g (0.277 mol) of diethyl methylmalonate (available from Aldrich Chem. Co., Catalog No. 12,613-6) in 60 ml of N1N-dimethyl formamide (DMF) is added dropwise to a stirred solution of 6.86 g (0.277 mol) of sodium hydride (NaH) in DMF. The reaction mixture is heated during the dropwise addition of a solution of 72.17 g (0.284 mol) of 1-bromododecane (Aldrich Chem. Co., catalog no. B6,555-1) in 60 ml DMF. The reaction is heated to 80° C. and stirred overnight, after which the NaBr that precipitated is filtered and the DMF removed in vacuo. The oily residue obtained is dissolved in ether and filtered again to remove all NaBr. The ether solution is washed with water followed by saturated NaCl. The solution is dried over anhydrous sodium sulfate and the ether is removed under reduced pressure to yield a clear, yellow oil. Fractional distillation (130°-138° C., 0.007 mm Hg) gives 82.28 g (88% overall yield) of diethyl dodecyl-methylmalonate as a clear oil. The oil is dissolved in 175 ml of anhydrous ether, and the solution is added dropwise to a suspension of 19.21 g (0.480 mol) of lithium aluminum hydride. The reaction is stirred overnight, carefully quenched, and filtered. The solvent is removed in vacuo and the solid obtained is recrystallized and dried to give 51.00 g (81% overall yield) of 2-dodecyl-2-methylpropane-1,3-diol as a white solid (mp 67°-68° C.).

Provenance & Evidence