Water → p-Hydroxystyrene p-tetrahydropyranyloxystyrene

HRID 1600497Notes

Reaction equation

HRID 1600497 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.N1C=CC=[CH:9][CH:8]=1.[C:13]1([CH3:23])[CH:18]=[CH:17][C:16](S(O)(=O)=O)=[CH:15][CH:14]=1.[OH2:24]>O1CCOCC1>[OH:1][C:6]1[CH:5]=[CH:4][C:3]([CH:8]=[CH2:9])=[CH:2][CH:13]=1.[O:24]1[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[O:1][C:16]1[CH:17]=[CH:18][C:13]([CH:23]=[CH2:8])=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyran

Product 1

HCID 67686066p-Hydroxystyrene p-tetrahydropyranyloxystyrene

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 10.8 g of poly(p-hydroxystyrene) obtained according to (2) in 72 ml of 1,4-dioxane were added 1.2 g of 2,3-dihydropyran and 0.05 g of pyridine salt of p-toluenesulfonic acid to carry out reaction at 25-30° C. for 15 hours. The reaction solution was poured into 1,000 ml of water and crystallized. Precipitated crystals were filtered out, washed with water and dried in vacuo to give 10.0 g of poly(p-hydroxystyrene/p-tetrahydropyranyloxystyrene) as white powdery crystal. P-hydroxystyrene unit/p-tetrahydropyranyloxystyrene unit molar ratio in the polymer≈95:5 (1H NMR). Mw≈13,000 (GPC with polystyrene calibration).

Workup

  1. customreaction at 25-30° C. for 15 hours
  2. customcrystallized
  3. customPrecipitated crystals
  4. filtrationwere filtered out
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-95066e95bedc49e1b62dee08132baa8f
Source dataset
uspto-grants-1999_11
Patent number
US05976759

Reaction notes

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