Water → 4-Ethynylphenol

HRID 1530155Notes

Reaction equation

HRID 1530155 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.N(C(C)(C)C#N)=NC(C)(C)C#N.[OH-].[Na+].O>C(OCCCC)(=O)C.CCCCCC>[CH:10]#[C:9][C:8]1[CH:11]=[CH:12][C:5]([OH:4])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 6547AzobisisobutyronitrileHCID 14798Sodium HydroxideHCID 758214-Ethenylphenyl acetate

Product 1

HCID 327584-Ethynylphenol

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 31272Butyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

p-Acetoxystyrene (32.4 g (0.2 mol)) was dissolved in 120 ml of butyl acetate, 0.066 g of azobisisobutyronitrile (AIBN) was added thereto with stirring at 80° C. three times every 2.5 hours in a nitrogen stream, and the stirring was further continued for 5 hours, thereby performing the polymerization reaction. The reaction solution was poured in 1,200 ml of hexane to precipitate a white resin, and the obtained resin was dried and then dissolved in 150 ml of methanol. An aqueous solution containing 7.7 g (0.19 mol) of sodium hydroxide/50 ml of water was added thereto, and the resulting solution was refluxed under heating for 3 hours to effect hydrolysis. The resulting reaction solution was diluted by adding 200 ml of water and neutralized with hydrochloric acid to precipitate a white resin. The precipitated resin was separated by filtration, washed with water, dried and further dissolved in 200 ml of tetrahydrofuran, and the resulting solution was added dropwise to 5 L of ultrapure water with vigorous stirring, thereby effecting reprecipitation. This reprecipitation operation was repeated three times. The obtained resin was dried in a vacuum drier at 120° C. for 12 hours to obtain poly(p-hydroxystyrene) Alkali-Soluble Resin R-1. The weight average molecular weight of the obtained resin was 3,000.

Workup

  1. waitthe stirring was further continued for 5 hours
  2. customthe polymerization reaction
  3. customto precipitate a white resin
  4. customthe obtained resin was dried
  5. dissolutiondissolved in 150 ml of methanol
  6. additionwas added
  7. temperaturethe resulting solution was refluxed
  8. temperatureunder heating for 3 hours
  9. customhydrolysis
  10. customThe resulting reaction solution
  11. additionwas diluted
  12. customneutralized with hydrochloric acid to precipitate a white resin
  13. customThe precipitated resin was separated by filtration
  14. washwashed with water
  15. customdried
  16. dissolutionfurther dissolved in 200 ml of tetrahydrofuran
  17. additionthe resulting solution was added dropwise to 5 L of ultrapure water with vigorous stirring
  18. customreprecipitation
  19. customThe obtained resin was dried in a vacuum drier at 120° C. for 12 hours

Sources & evidence

ORD record
ord-37e2b97223b443d6a4722a3d1a89961c
Source dataset
uspto-grants-2015_07
Patent number
US09090722B2

Reaction notes

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