4-Hydroxybenzoic Acid → 4-(6-Hydroxyhexyloxy)benzoic acid

Participants

Reaction Steps

229.2 g (1.66 mol) of p-hydroxy-benzoic acid were dissolved in 600 ml of methanol and treated at 0° C. within 10 minutes with a solution of 151 g (3.77 mol) of NaOH in 480 ml of H2O. 271.2 g (1.99 mol) of 6-chloro-hexanol were slowly added dropwise to this solution. Finally, 0.75 g of potassium iodide was added and the batch was boiled under reflux for 60 hours. For the working up, the yellow solution was poured into 3 1 of H2O and treated with 10% HCl (about 600 ml) until a pH value of 1 had been achieved. The milky suspension was filtered over a large suction filter. The residue was sucked dry and recrystallized twice from about 1.5 l of ethanol. This gave 229.6 g of 4-(6-hydroxy-hexyloxy)-benzoic acid as a fine white powder; m.p. 136-141° C.

Provenance & Evidence