Acetic Acid → p-Hydroxystyrene p-tert-butoxystyrene

HRID 1600506Notes

Reaction equation

HRID 1600506 reaction equation
C([O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[CH2:10])=[CH:7][CH:6]=1)(=O)C.[C:13]([O:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=[CH2:23])=[CH:20][CH:19]=1)([CH3:16])([CH3:15])[CH3:14].[OH-].C[N+](C)(C)C.C(O)(=O)C>C(O)(C)C>[OH:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[CH2:10])=[CH:7][CH:6]=1.[C:13]([O:17][C:18]1[CH:19]=[CH:20][C:21]([CH:22]=[CH2:23])=[CH:24][CH:25]=1)([CH3:16])([CH3:14])[CH3:15]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 60966Tetramethylammonium hydroxideHCID 86754729p-Acetyloxystyrene p-tert-butoxystyrene

Product 1

HCID 68598693p-Hydroxystyrene p-tert-butoxystyrene

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 46.3 g of poly(p-acetyloxystyrene/p-tert-butoxystyrene) obtained according to (1) above and 100 ml of a 16% aqueous solution of tetramethylammonium hydroxide was refluxed with stirring in 300 ml of isopropanol for 4 hours. The reaction solution was neutralized with acetic acid and concentrated under reduced pressure, and the residue was dissolved in 150 ml of acetone and poured into 5,000 ml of water to cause crystallization. Precipitated crystals were filtered out, washed with water and dried in vacuo to give 33.8 g of poly(p-hydroxystyrene/p-tert-butoxystyrene). P-hydroxystyrene unit/p-tert-butoxystyrene unit molar ratio in the polymer≈3:1 (1HNMR). Mw≈8,540; Mw/Mn=1.30 (GPC with polystyrene calibration).

Workup

  1. customobtained
  2. temperaturewas refluxed
  3. concentrationconcentrated under reduced pressure
  4. dissolutionthe residue was dissolved in 150 ml of acetone
  5. additionpoured into 5,000 ml of water
  6. customcrystallization
  7. customPrecipitated crystals
  8. filtrationwere filtered out
  9. washwashed with water
  10. customdried in vacuo

Sources & evidence

ORD record
ord-7a2e5da259204190be7fc49dc0104e2a
Source dataset
uspto-grants-1999_11
Patent number
US05976759

Reaction notes

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