4-Ethenylphenyl acetate → 4-Vinylphenol

HRID 1468601Notes

Reaction equation

HRID 1468601 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.C[O-].[Na+]>C(OCC)(=O)C>[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 758214-Ethenylphenyl acetateHCID 10942334Sodium Methoxide

Product 1

HCID 624534-VinylphenolYield 54%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
0 °C

Procedure

First, 100.00 parts by mass of p-acetoxystyrene was dissolved in 400 parts by mass of ethyl acetate, and cooled to 0° C. Subsequently, 47.60 parts by mass of sodium methoxide (28% methanol solution) was dropped into the cooled solution over a period of 30 minutes, and agitated at room temperature for five hours. Ethyl acetate was added, and the resultant organic phase was washed with distilled water thrice. The washed organic phase was dried over anhydrous sodium sulfate, and the solvent was distilled off. Thus, 131.70 parts by mass of p-hydroxystyrene (54% ethyl acetate solution) was obtained.

Workup

  1. washthe resultant organic phase was washed with distilled water thrice
  2. dry with materialThe washed organic phase was dried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-188d4d64134d43439519fe64d4390b48
Source dataset
uspto-grants-2015_04
Patent number
US09005870B2

Reaction notes

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