Hydrochloric Acid → 4-Ethynylphenol

HRID 986898Notes

Reaction equation

HRID 986898 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+].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

Procedure

32.4 g (0.2 mol) of p-acetoxystyrene was dissolved in 120 ml of butyl acetate and thereto, 0.033 g of azobisisobutyronitrile (AIBN) was added at 80° C. while stirring in a nitrogen stream 3 times every 2.5 hours. The stirring was further continued for 5 hours to perform the polymerization reaction. The reaction solution was charged into 1,200 ml of hexane and white resin was precipitated. The resin obtained was dried and then dissolved in 150 ml of methanol and thereto, an aqueous solution of 7.7 g (0.19 mol) of sodium hydroxide/50 ml of water was added. The mixed solution was heated under reflux for 3 hours to perform the hydrolysis, then diluted by adding 200 ml of water, and neutralized with hydrochloric acid to precipitate white resin. This resin was separated by filtration, washed with water, and dried. The resulting resin was dissolved in 200 ml of tetrahydrofuran. The resulting solution was added dropwise to 5 L of ultrapure water while vigorously stirring to reprecipitate the resin. This reprecipitation operation was repeated 3 times and the resin obtained was dried in a vacuum dryer at 120° C. for 12 hours to obtain poly(p-hydoxystyrene) Alkali-Soluble Resin R-1.

Workup

  1. waitThe stirring was further continued for 5 hours
  2. customthe polymerization reaction
  3. customwas precipitated
  4. customThe resin obtained
  5. customwas dried
  6. dissolutiondissolved in 150 ml of methanol
  7. temperatureThe mixed solution was heated
  8. temperatureunder reflux for 3 hours
  9. customthe hydrolysis
  10. additiondiluted
  11. customto precipitate white resin
  12. customThis resin was separated by filtration
  13. washwashed with water
  14. customdried
  15. dissolutionThe resulting resin was dissolved in 200 ml of tetrahydrofuran
  16. additionThe resulting solution was added dropwise to 5 L of ultrapure water
  17. stirringwhile vigorously stirring
  18. customthe resin obtained
  19. customwas dried in a vacuum dryer at 120° C. for 12 hours

Sources & evidence

ORD record
ord-e20ec1737091413a854ed8eda01a0851
Source dataset
uspto-grants-2003_10
Patent number
US06630280B1

Reaction notes

Loading…