Hydrochloric Acid → 4-Ethynylphenol

Temperature

80 °C

In 120 ml of butyl acetate was dissolved 32.4 g (0.2 mol) of p-acetoxystyrene. To the solution was then added 0.033 g of azobisisobutylonitrile (AIBN) with stirring in a stream of nitrogen at a temperature of 80° C. every 2.5 hours three times in all. Thereafter, the mixture was stirred for 5 hours to undergo a polymerization reaction. The reaction solution was then poured into 1,200 ml of hexane to cause the precipitation of a white resin. The resin thus obtained was dried, and then dissolved in 150 ml of methanol. To the solution was added a solution of 7.7 g (0.19 mol) of sodium hydroxide in 50 ml of water. The reaction solution was then heated under reflux for 3 hours to undergo hydrolysis. Thereafter, the reaction solution was diluted with 200 ml of water, and then neutralized with hydrochloric acid to cause the precipitation of a white resin. The resin thus obtained was collected by filtration, washed with water, and dried. The resin thus obtained was dissolved in 200 ml of tetrahydrofuran, and added dropwise to 5 liters of ultrapure water with vigorous stirring to reprecipitate. The reprecipitation procedure was then repeated three times. The resin thus obtained was dried at a temperature of 120° C. in a vacuum drier for 12 hours to obtain a poly(p-hydroxystyrene) alkali-soluble resin R-1.

1. stirringThereafter, the mixture was stirred for 5 hours
2. customa polymerization reaction
3. customthe precipitation of a white resin
4. customThe resin thus obtained
5. customwas dried
6. dissolutiondissolved in 150 ml of methanol
7. temperatureThe reaction solution was then heated
8. temperatureunder reflux for 3 hours
9. customhydrolysis
10. customthe precipitation of a white resin
11. customThe resin thus obtained
12. filtrationwas collected by filtration
13. washwashed with water
14. customdried
15. customThe resin thus obtained
16. stirringwith vigorous stirring
17. customThe reprecipitation procedure
18. customThe resin thus obtained
19. customwas dried at a temperature of 120° C. in a vacuum drier for 12 hours

ORD record

ord-a6364b4641db43e4aec315d08aaa713b

Source dataset

uspto-grants-2002_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06376152B2