4-Vinylphenol → p-1-Ethoxyethoxystyrene p-hydroxystyrene

HRID 743944Notes

Reaction equation

C(O[CH:4]([O:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[CH2:12])=[CH:9][CH:8]=1)[CH3:5])C.[OH:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=[CH2:21])=[CH:18][CH:17]=1>>[CH2:16]([O:15][CH2:5][CH2:4][O:6][C:7]1[CH:8]=[CH:9][C:10]([CH:11]=[CH2:12])=[CH:13][CH:14]=1)[CH3:17].[OH:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=[CH2:21])=[CH:18][CH:17]=1

Participants

Reactant 2

HCID 624534-Vinylphenol

HCID 9855712p-(1-Ethoxyethoxy)styrene

Product 1

HCID 131719558p-1-Ethoxyethoxystyrene p-hydroxystyrene

Procedure

To a solution of poly(p-hydroxystyrene) (4.0 g) obtained in above (2) and ethyl vinyl ether (1.2 g) in a mixed solvent (35 ml) of 1,4-dioxane and pyridine, a catalytic amount of p-toluenesulfonic acid was added and reacted with stirring at room temperature for 24 hours. The reaction mixture was poured into H2O (1 l) and a white solid was precipitated. The polymer was filtered, washed with h2O and dried under reduced pressure to afford 5.0 g of poly[p-(1-ethoxyethoxy)styrene/p-hydroxystyrene] as white powder having Mw 10000 (GPC with polystyrene calibration). The polymer was found to have p-(1-ethoxyethoxy)styrene unit and p-hydroxystyrene unit in a molar ratio of ca. 4:6 based on 1HNMR.

Sources & evidence

ORD record: ord-7dffbb8f5fef4ce5bcf13d6e60ecfda2
Source dataset: uspto-grants-1996_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05558976

Reaction notes

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