Water → 10-Propoxydecanoic acid

Participants

Reaction Conditions

Reaction Steps

10-bromodecanoic acid (1 g, 3.98 mmol) was added to a solution of potassium hydroxide (0.893 g, 15.9 mmol) in n-propanol (30 mL) and stirred at 102° C. for 18 hrs. The reaction was allowed to cool to room temperature after the addition of 20 mL water. After acidification to pH=1 and extraction into ethyl acetate, the organic phase was dried over sodium sulfate and solvent removed at reduced pressure to yield a yellow oil. The product was purified by silica column chromatography in 2% diethyl ether/methylene chloride/0.2% formic acid, and then in 7% ethyl acetate/hexane/0.3% formic acid. Recrystallization from hexane at -20° C. yielded 10-(propoxy)decanoic acid (74 mg, 12%): mp <30° C.; 1H NMR (300 MHz, CDCl3) δ 0.91 (t, 3H, J=7.5, CH3), 1.18-1.40 (br, 10H, methylene envelope), 1.48-1.67 (bm, 6H, CH3CH2CH2OCH2CH2, CH2CH2COOH), 2.33 (t, 2H, J=7.4, CH2COOH), 3.31-3.45 (bm, 4H, CH2OCH2), 10.37 (br, 1H COOH); 13C NMR (75.4 MHz, CDCl3) 10.67, 22.94, 24.72, 26.19, 29.09, 29.22, 29.41, 29.74, 34.11, 70.88, 72.53, 179.69; m/z 231 (M+H).

Provenance & Evidence