Sulfuric Acid → p-Hydroxystyrene p-tetrahydropyranyloxystyrene

HRID 2674

Reaction equation

HRID 2674 reaction equation
[CH:1]#[C:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[O:10]1[CH:15]=[CH:14][CH2:13][CH2:12][CH2:11]1.S(=O)(=O)(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.O>[O:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]1[O:9][C:6]1[CH:7]=[CH:8][C:3]([CH:2]=[CH2:1])=[CH:4][CH:5]=1.[OH:9][C:6]1[CH:7]=[CH:8][C:3]([CH:2]=[CH2:1])=[CH:4][CH:5]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 80803,4-dihydro-2H-pyranHCID 10340Sodium CarbonateHCID 327584-Ethynylphenol

Product 1

HCID 67686066p-Hydroxystyrene p-tetrahydropyranyloxystyrene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Poly(p-hydroxystyrene) (weight average molecular weight: 9,600) in an amount of 9 g was dissolved in 100 ml of dimethoxyethane, and thereto 12.6 g of 3,4-dihydro-2H-pyran and 0.5 ml of sulfuric acid were added. This solution was stirred for 15 hours at 30°-40° C. After the reaction was completed, the reaction solution was concentrated under reduced pressure. The residue obtained was neutralized with sodium carbonate, and then poured into water to precipitate crystals. The crystals were filtered off, washed with water and dried under reduced pressure. Thus, 11.0 g of poly(p-tetrahydropyranyloxystyrene-p-hydroxystyrene) was obtained as white powder. The ratio of the p-tetrahydropyranyloxystyrene units to the p-hydroxystyrene units in the polymer obtained was determined to be 3:7 by 1H-NMR analysis.

Workup

  1. concentrationthe reaction solution was concentrated under reduced pressure
  2. customThe residue obtained
  3. customto precipitate crystals
  4. filtrationThe crystals were filtered off
  5. washwashed with water
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-5a412429988a4f6d803dc50ce52e1efd
Source dataset
uspto-grants-1998_03
Patent number
US05731123

Linked notes

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