Sulfuric Acid → p-Tetrahydropyranylstyrene p-hydroxystyrene

HRID 1378896Notes

Reaction equation

HRID 1378896 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(COC)OC>[O:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH:15]1[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

5

Reactant 3

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

Product 1

HCID 131719203p-Tetrahydropyranylstyrene p-hydroxystyreneYield 93.6%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of poly(p-hydroxystyrene) (9.0 g) [MARUKA LYNCUR-M, manufactured by Maruzen Petrochemical Co., Ltd., Mw 10000 and Mn 5000] in dimethoxyethane (100 ml), 3,4-dihydro-2H-pyran (12.6 g) and conc. sulfuric acid (0.5 ml) were added, followed by reaction at 30°-40° C. for 15 hours with stirring. After reaction, the mixture was evaporated in vacuo, the residue was neutralized by addition of sodium carbonate and poured into H2O (1 liter). The precipitate was filtered by suction, washed with H2O and dried under reduced pressure to give 11.0 g of the title compound as a white powder having Mw 10000 (GPC with polystyrene calibration). The composition of the polymer was found to be p-tetrahydro-pyranyloxystyrene unit and p-hydroxystyrene unit in a molar ratio of ca. 3:7 based on 1HNMR.

Workup

  1. customfollowed by reaction at 30°-40° C. for 15 hours
  2. customAfter reaction
  3. customthe mixture was evaporated in vacuo
  4. additionthe residue was neutralized by addition of sodium carbonate
  5. additionpoured into H2O (1 liter)
  6. filtrationThe precipitate was filtered by suction
  7. washwashed with H2O
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-dd98096ba2124c9fb32aaa8e39e3b966
Source dataset
uspto-grants-1997_09
Patent number
US05670299

Reaction notes

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