Sodium Hydroxide → HCID 86691651, compound

Participants

Reaction Conditions

Reaction Steps

Diethyl 2-(12-(1H-imidazol-1-yl)hexadecyl)malonate (415 mg, 0.9209 mmol) was dissolved in a 3:1 mixture of methanol (9 ml) and water (3 ml), cooled to 0° C. then NaOH (147 mg, 3.684 mmol) was added and the reaction mixture stirred at room temperature for 3 h. The reaction mixture was then concentrated under reduced pressure to remove MeOH, cooled to 0° C. to 5° C., the pH adjusted to 5, extracted with DCM (3×25 ml), dried on dry MgSO4, and concentrated under reduced pressure. The crude compound was obtained as a light yellow color liquid. This crude compound was heated at 170° C. to remove one carboxyl acid group from the di-carboxylic acid by the evolution of CO2. The crude product was then purified by silica gel column (3 to 5% of MeOH in DCM) to give 14-(1H-imidazol-1-yl)octadecanoic acid (221 mg, 68%) as a pale yellow gummy liquid.

Provenance & Evidence