4-Hydroxybenzoic Acid → 4-((6-(Acryloyloxy)hexyl)oxy)benzoic acid

Participants

Reaction Steps

In a 500 ml three-necked flask were placed 33.2 g of p-hydroxybenzoic acid, 54.3 g of 6-bromohexanol, 41.5 g of potassium carbonate and 200 ml of N,N-dimethylacetamide, and were vigorously stirred at 120° C. for 5 hours with a mechanical stirrer. After the obtained reaction mixture was cooled, it was poured in 200 ml of water, and the mixture was extracted with 500 ml of ethyl acetate, and then the extract was washed with two portions of 100 ml of water. The obtained extract was dried by mixing with anhydrous magnesium sulfate and filtered. The filtrate was concentrated by evaporating the solvent in vacuo, and the resultant residue was dissolved in 100 ml of methanol. Then, a methanol solution (20 ml) containing potassium hydroxide of 16.8 g was dropwise added to the methanol solution and heated under reflux for 2 hour. The resultant reaction mixture was cooled, the precipitated crystals were filtered, and the residue was dissolved in 1 liter of water. 25.7 ml of concentrated hydrochloric acid was added to the solution, and the precipitated crystals were filtered and washed with water. The residue was dried to obtain the 4-(6-hydroxyhexyloxy)benzoic acid of 61.5 g (yield: 86%).

Provenance & Evidence