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

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%).

1. customIn a 500 ml three-necked flask were placed
2. customAfter the obtained reaction mixture
3. temperaturewas cooled
4. extractionthe mixture was extracted with 500 ml of ethyl acetate
5. washthe extract was washed with two portions of 100 ml of water
6. extractionThe obtained extract
7. customwas dried
8. additionby mixing with anhydrous magnesium sulfate
9. filtrationfiltered
10. concentrationThe filtrate was concentrated
11. customby evaporating the solvent in vacuo
12. dissolutionthe resultant residue was dissolved in 100 ml of methanol
13. additionThen, a methanol solution (20 ml) containing potassium hydroxide of 16.8 g
14. additionwas dropwise added to the methanol solution
15. temperatureheated
16. temperatureunder reflux for 2 hour
17. customThe resultant reaction mixture
18. temperaturewas cooled
19. filtrationthe precipitated crystals were filtered
20. dissolutionthe residue was dissolved in 1 liter of water
21. addition25.7 ml of concentrated hydrochloric acid was added to the solution
22. filtrationthe precipitated crystals were filtered
23. washwashed with water
24. customThe residue was dried

ORD record

ord-0e52a4152b73442097c0e658da7fb76a

Source dataset

uspto-grants-1997_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05635105