Methanol → 11-Methoxyundecanoic acid

Participants

Reaction Steps

11-bromoundecanoic acid (10.0 g, 37.7 mmol) was added to a solution of potassium hydroxide (24.3 g, 433 mmol) in methanol (280 mL) and refluxed for 5 hrs. After cooling and acidification with HCl, solvent was removed under reduced pressure. The sample was dissolved in ethyl acetate and extracted with water. The organic phase was dried over sodium sulfate, and the solvent removed under reduced pressure. The product was purified by silica column chromatography using increasing concentrations of ethyl acetate in hexanes for elution. The product eluted in 25% ethyl acetate in hexanes. Solvent was removed under reduced pressure to give 11-(methoxy)undecanoic acid (200 mg, 2.5%): mp 31-32° C.; 1H NMR (300 MHz, CDCl3) δ1.1-1.3 (bm, 12H, methylene envelope), 1.45-1.63 (bm, 4H, O--CH2 --CH2, CH2 --CH2 --COOH), 2.34 (t, 2H, J=7.3, CH2 --COOH), 3.45 (s, 3H, CH3), 3.50 (t, 2H, J=6.8, 0--CH2), 10.70 (br, COOH); 13C NMR (75.4 MHz, CDCl3) δ24.64, 26.00, 29.00, 29.16, 29.29, 29.40, 34.00, 58.23, 72.81, 179.17; m/z 216 (M+).

Provenance & Evidence