Potassium Hydroxide → 4-Vinylphenol

HRID 1938137Notes

Reaction equation

HRID 1938137 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-].[K+]>O>[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 14797Potassium HydroxideHCID 758214-Ethenylphenyl acetate

Product 1

HCID 624534-VinylphenolYield 59.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

p-Hydroxyacetophenone was converted to 1-(p-acetoxyphenyl)ethanol and then dehydrated using liquid phase dehydration in the presence of potassium acid sulfate to produce p-acetoxystyrene, according to the method of Corson et al (J. Org. Chem., 1958 23, 544). p-Acetoxystyrene (1.6 g) was added to a stirred solution of potassium hydroxide (1.4 g) in water (14 ml) at 5 degrees Centigrade. Stirring was continued at 0-5 degrees Centigrade for 2 h. The mixture was then washed with ether, and the aqueous phase neutralised with saturated sodium hydrogen carbonate solution. The product was extracted into dichloromethane, the solution was dried over anhydrous calcium chloride and the solvent removed, to yield a cloudy oil (0.7 g) which solidified on standing to a waxy solid.

Workup

  1. washThe mixture was then washed with ether
  2. extractionThe product was extracted into dichloromethane
  3. dry with materialthe solution was dried over anhydrous calcium chloride
  4. customthe solvent removed

Sources & evidence

ORD record
ord-1bccda7236464bf2b53834ae31b31ad3
Source dataset
uspto-grants-1997_12
Patent number
US05693477

Reaction notes

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