Water → p-(1-Ethoxy ethoxy)styrene p-hydroxystyrene

HRID 129363

Reaction equation

HRID 129363 reaction equation
[CH:1]#[C:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[CH:10]([O:12][CH2:13][CH3:14])=[CH2:11].O>O1CCOCC1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[CH2:10]([O:12][CH:13]([O:9][C:6]1[CH:7]=[CH:8][C:3]([CH:2]=[CH2:1])=[CH:4][CH:5]=1)[CH3:14])[CH3:11].[OH:9][C:6]1[CH:7]=[CH:8][C:3]([CH:2]=[CH2:1])=[CH:4][CH:5]=1

Participants

6

Reactant 3

HCID 962WaterHCID 8023Ethyl vinyl etherHCID 327584-Ethynylphenol

Product 1

HCID 67610320p-(1-Ethoxy ethoxy)styrene p-hydroxystyreneYield 94.5%

Reagents, catalysts & solvents 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of poly(p-hydroxystyrene) (8.0 g) [MARUKA LYNCUR-M, manufactured by Maruzene Petrochemical Co., Ltd., having Mw 10000 and Mn 5000], ethyl vinyl ether (3.0 g) and pyridinium p-toluenesulfonate (0.5 g) in dioxane (70 ml) was reacted with stirring at room temperature for 24 hours. After reaction, the mixture was poured into H2O, was precipitated with stirring, and the precipitate was filtered, washed with H2O and then dried in vacuo. There was obtained 10.0 g of the desired product as a white powder having Mw 11000 (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. 1:1 based on 1HNMR.

Workup

  1. customAfter reaction
  2. customwas precipitated
  3. stirringwith stirring
  4. filtrationthe precipitate was filtered
  5. washwashed with H2O
  6. customdried in vacuo

Sources & evidence

ORD record
ord-f82e1058d1564f108a6e4692f55f5f39
Source dataset
uspto-grants-1995_11
Patent number
US05468589

Linked notes

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