Ammonium Hydroxide → 4-Vinylphenol

HRID 1602754Notes

Reaction equation

HRID 1602754 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.[OH-].[NH4+]>C1COCC1>[OH:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[CH2:10])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 758214-Ethenylphenyl acetate

Product 1

HCID 624534-Vinylphenol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-Acetoxystyrene (105 grams, 0.65 mole) in THF (400 ml) was stirred at room temperature with 14.8 Molar ammonium hydroxide (52 ml, 0.77 mole) for 18 hours. Afterward, the solution was washed three times with brine (250 ml) and dried over anhydrous magnesium sulfate. Solvent was removed in a rotary evaporator and the viscous liquid was dried under high vacuum for 24 hours to give a waxy solid. Typically, this waxy solid is around 90% pure (by NMR), remainder being THF.

Workup

  1. washAfterward, the solution was washed three times with brine (250 ml)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customSolvent was removed in a rotary evaporator
  4. customthe viscous liquid was dried under high vacuum for 24 hours
  5. customto give a waxy solid

Sources & evidence

ORD record
ord-73335b8439614c1f835d94d7af15779a
Source dataset
uspto-grants-1999_11
Patent number
US05985524

Reaction notes

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