4-Hydroxybenzoic Acid → 4-(3-Hydroxypropoxy)benzoic acid

Participants

Reaction Steps

To a solution of 4-hydroxybenzoic acid (25.0 g, 0.18 mol), potassium hydroxide (27.6 g, 0.49 mol), and potassium iodide (3.0 g, 0.018 mol) in ethanol (75 mL) and water (5 mL) was added dropwise 3-bromopropanol (25.6 g, 0.19 mol). The reaction was allowed to continue for 24 h under reflux. The solid residue was filtered off, and the filtrate was evaporated to dryness. The resultant solid was dissolved in water (200 mL) and then acidified with a 10% HCl solution. The precipitate was filtered for recrystallization from ethanol: water (1:1) to yield 1(26.7 g, 75%). 1H NMR (200 MHz, DMSO-d6): δ 1.85 (quintet, 2H, —CH2—), δ 3.55 (t, 2H, —CH2OAr), δ 4.10 (t, 2H, HOCH2—), δ 6.95 (d, 2H, aromatic ring), δ 7.85 (d, 2H, aromatic ring).

Provenance & Evidence