Water → p-Hydroxystyrene p-tetrahydropyranyloxystyrene

HRID 430910Notes

Reaction equation

HRID 430910 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.[C:7]1([CH3:17])[CH:12]=[CH:11][C:10](S([O-])(=O)=O)=[CH:9][CH:8]=1.[NH+]1C=CC=C[CH:19]=1.[OH2:24]>O1CCOCC1>[OH:1][C:6]1[CH:5]=[CH:4][C:3]([CH:7]=[CH2:8])=[CH:2][CH:19]=1.[O:24]1[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[O:1][C:10]1[CH:11]=[CH:12][C:7]([CH:17]=[CH2:19])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Product 1

HCID 67686066p-Hydroxystyrene p-tetrahydropyranyloxystyrene

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

10.8 Grams of poly(p-hydroxystyrene) obtained in above (2) was dissolved in 72 ml of 1,4-dioxane, and 2.5 g of 3,4-dihydro-2H-pyrane and 0.05 g of pyridinium p-toluenesulfonate were added thereto, followed by conducting a reaction at 25 to 30° C. for 15 hours with stirring. The reaction solution is poured into 1000 ml of water to precipitate out. The precipitated polymer was filtered, washed with water and dried under reduced pressure to give 10.0 g of poly(p-hydroxystyrene/p-tetrahydropyranyloxystyrene) as white powders. A ratio of p-hydroxystyrene unit and p-tetrahydropyranyloxystyrene unit was about 90:10 by 1HNMR. Mw: about 15500, Mw/Mn: 1.18 (GPC method: polystyrene as standard).

Workup

  1. customa reaction at 25 to 30° C. for 15 hours
  2. customto precipitate out
  3. filtrationThe precipitated polymer was filtered
  4. washwashed with water
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-8211969ecfe94fe4ac6a79659cf5c4e6
Source dataset
uspto-grants-2003_12
Patent number
US06656660B1

Reaction notes

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