Hydrochloric Acid → 4-Vinylphenol

HRID 1926559Notes

Reaction equation

HRID 1926559 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.CO.COCC(O)C.Cl>O>[OH:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[CH2:10])=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 79001-Methoxy-2-propanolHCID 758214-Ethenylphenyl acetate

Product 1

HCID 624534-VinylphenolYield 98.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

In a reaction vessel, 40.00 g of the obtained 4-acetoxystyrene polymer (with main chain terminal (M-30)), 40 ml of methanol, 100 ml of 1-methoxy-2-propanol and 1.5 ml of concentrated hydrochloric acid were added, and the mixture was stirred for 5 hours under heating at 80° C. The reaction solution was allowed to cool to room temperature and then added dropwise to 3 L of distilled water. After dissolving the solid collected by filtration in 200 ml of acetone, the solution was again added dropwise to 3 L of distilled water, and the solid was collected by filtration and then dried under reduced pressure to obtain 29.31 g of a 4-hydroxystyrene polymer (with main chain terminal (M-14)). The weight average molecular weight by GPC was 15,000, and the molecular weight dispersity (Mw/Mn) was 1.55.

Workup

  1. temperatureto cool to room temperature
  2. dissolutionAfter dissolving the solid
  3. filtrationcollected by filtration in 200 ml of acetone
  4. additionthe solution was again added dropwise to 3 L of distilled water
  5. filtrationthe solid was collected by filtration
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-5a27d0171ba043a3bbd17bc3d5e6db31
Source dataset
uspto-grants-2012_05
Patent number
US08182975B2

Reaction notes

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