Hydrochloric Acid → p-1-Ethoxyethoxystyrene p-hydroxystyrene p-tert-butoxystyrene

HRID 1636200

Reaction equation

HRID 1636200 reaction equation
Cl.[OH:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[CH2:8])=[CH:5][CH:4]=1.[C:11]([O:15][C:16]1C=CC(C=C)=C[CH:17]=1)(C)(C)[CH3:12].[OH:24][C:25]1[CH:32]=[CH:31][C:28]([CH:29]=[CH2:30])=[CH:27][CH:26]=1.[C:33]([O:37][C:38]1[CH:45]=[CH:44][C:41]([CH:42]=[CH2:43])=[CH:40][CH:39]=1)([CH3:36])([CH3:35])[CH3:34]>C(O)(C)C.O>[CH2:11]([O:15][CH2:16][CH2:17][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[CH2:8])=[CH:5][CH:4]=1)[CH3:12].[OH:24][C:25]1[CH:32]=[CH:31][C:28]([CH:29]=[CH2:30])=[CH:27][CH:26]=1.[C:33]([O:37][C:38]1[CH:39]=[CH:40][C:41]([CH:42]=[CH2:43])=[CH:44][CH:45]=1)([CH3:36])([CH3:34])[CH3:35]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 624534-VinylphenolHCID 5775311-(Tert-butoxy)-4-ethenylbenzeneHCID 68598693p-Hydroxystyrene p-tert-butoxystyrene

Product 1

HCID 131721427p-1-Ethoxyethoxystyrene p-hydroxystyrene p-tert-butoxystyrene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

Poly(p-tert-butoxystyrene) obtained in the same manner as described in Production Example 1(1) in an amount of 15.0 g was suspended in isopropanol and added with 15 ml of concentrated hydrochloric acid. The reaction was carried out at 70° to 80° C. for 4 hours with stirring. After cooling, the reaction solution was poured into 1000 ml of water to deposit crystals. The deposited crystals were filtered, washed with water and dried under reduced pressure to give 9.4 g of white powdered crystals of poly(p-hydroxystyrene/p-tert-butoxystyrene). The proportion of the p-hydroxystyrene unit and the p-tert-butoxystyrene unit of the obtained polymer was about 30:64:6 measured by 1H NMR. Mw was about 17,500 and the degree of dispersion was 1.16 (GPC method, polystyrene standard).

Workup

  1. temperatureAfter cooling
  2. filtrationThe deposited crystals were filtered
  3. washwashed with water
  4. customdried under reduced pressure
  5. customto give 9.4 g

Sources & evidence

ORD record
ord-cb49ff37dc9b429a91025d15adc62fb4
Source dataset
uspto-grants-2000_03
Patent number
US06033826

Linked notes

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