Hydrochloric Acid → 4-Ethynylphenol

HRID 2086525Notes

Reaction equation

HRID 2086525 reaction equation
C([O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[CH2:10])=[CH:7][CH:6]=1)(=O)C.CC(N=NC(C#N)(C)C)(C#N)C.[OH-].[Na+].Cl>C(OCCCC)(=O)C.O.CCCCCC>[CH:10]#[C:9][C:8]1[CH:11]=[CH:12][C:5]([OH:4])=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6547AzobisisobutyronitrileHCID 14798Sodium HydroxideHCID 758214-Ethenylphenyl acetate

Product 1

HCID 327584-Ethynylphenol

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8058HexaneSolventHCID 31272Butyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

In 120 ml of butyl acetate was dissolved 32.4 g (0.2 mols) of p-acetoxystyrene, and to the resulting solution was added three times every 2.5 hours 0.033 g of azobisisobutylonitrile (AIBN) while stirring in a nitrogen gas stream at 80° C. Then, the mixture was further stirred for 5 hours to conduct a polymerization reaction. The reaction solution was poured into 1,200 ml of hexane to deposit a white resin. The resin obtained was dried and then dissolved in 150 ml of methanol. To the solution was added a solution of 7.7 g (0.19 mols) of sodium hydroxide dissolved in 50 ml of water and the reaction solution was heated under reflux for 3 hours to conduct hydrolysis. Then, the reaction solution was diluted by adding 200 ml of water and neutralized with hydrochloric acid to deposit a white resin. The resin was collected by filtration, washed with water and dried. The resin was then dissolved in 200 ml of tetrahydrofuran, and the resulting solution was added dropwise to 5 liters of ultrapure water with vigorous stirring to reprecipitate. The reprecipitation procedure was repeated three times. The resin obtained was dried at 120° C. in a vacuum drier for 12 hours to obtain poly(p-hydroxystyrene) as Alkali-Soluble Resin R-C1.

Workup

  1. stirringThen, the mixture was further stirred for 5 hours
  2. customa polymerization reaction
  3. customThe resin obtained
  4. customwas dried
  5. dissolutiondissolved in 150 ml of methanol
  6. temperaturethe reaction solution was heated
  7. temperatureunder reflux for 3 hours
  8. customhydrolysis
  9. additionThen, the reaction solution was diluted
  10. filtrationThe resin was collected by filtration
  11. washwashed with water
  12. customdried
  13. dissolutionThe resin was then dissolved in 200 ml of tetrahydrofuran
  14. additionthe resulting solution was added dropwise to 5 liters of ultrapure water
  15. stirringwith vigorous stirring
  16. customThe reprecipitation procedure
  17. customThe resin obtained
  18. customwas dried at 120° C. in a vacuum drier for 12 hours

Sources & evidence

ORD record
ord-956e638d1ba747848a31b90c0a49c075
Source dataset
uspto-grants-2004_04
Patent number
US06727033B2

Reaction notes

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