Potassium Hydroxide → 4-Vinylphenol

HRID 1769930Notes

Reaction equation

HRID 1769930 reaction equation
[OH-].[K+].C(OC([O:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[CH2:16])=[CH:13][CH:12]=1)=O)(C)(C)C>O.CO.[OH-].C[N+](C)(C)C>[CH:15]([C:14]1[CH:17]=[CH:18][C:11]([OH:10])=[CH:12][CH:13]=1)=[CH2:16]

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 934851,1-Dimethylethyl 4-ethenylphenyl carbonate

Product 1

HCID 624534-Vinylphenol

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 60966Tetramethylammonium hydroxideSolvent

Procedure

In a 2 L Erlenmeyer flask, 140 g (2.5 mol) of KOH was dissolved in 250 mL of water, and the solution was diluted with 250 mL of methanol and 10 mL of tetramethylammoniumhydroxide. Then, 110 g (0.50 mol) of 4-(t-butyloxycarbonyloxy)styrene (tBOCstyrene) was added and the mixture heated to boiling. After 5-8 minutes, the mixture cleared to a yellow solution and was cooled by the addition of 500 mL of a 1/1 ice-water mixture. This mixture was washed with 250 mL of dichloromethane and 250 mL of ethyl ether. The pH of the aqueous solution was reduced to 11-12 by the addition of dry ice, resulting in the formation of a cream colored precipitate (4-vinylphenol) in a yellow solution.

Workup

  1. temperaturethe mixture heated to boiling
  2. washThis mixture was washed with 250 mL of dichloromethane and 250 mL of ethyl ether
  3. additionThe pH of the aqueous solution was reduced to 11-12 by the addition of dry ice

Sources & evidence

ORD record
ord-9067fac39d9c4e4c820a49b02559b1c7
Source dataset
uspto-grants-1995_01
Patent number
US05384192

Reaction notes

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