Sulfuric Acid → p-Hydroxystyrene p-tert-butoxystyrene

HRID 1378897Notes

Reaction equation

HRID 1378897 reaction equation
[CH:1]#[C:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.S(=O)(=O)(O)O>C(COC)OC>[C:3]([O:9][C:6]1[CH:7]=[CH:8][C:3]([CH:2]=[CH2:1])=[CH:4][CH:5]=1)([CH3:8])([CH3:4])[CH3:2].[OH:9][C:6]1[CH:7]=[CH:8][C:3]([CH:2]=[CH2:1])=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 327584-Ethynylphenol

Product 1

HCID 68598693p-Hydroxystyrene p-tert-butoxystyrene

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of poly(p-hydroxystyrene) (4.0 g) [MARUKA LYNCUR-M, manufactured by Maruzen Petrochemical Co., Ltd., Mw 10000 and Mn 5000] in dimethoxyethane (70 ml) in a pressure vessel, isobutyrene (60 g) and conc. sulfuric acid (0.3 g) were added at -60° C. or lower. The mixture was brought to 45° C. for 1 hour with stirring, and then stirring was continued at room temperature for 22 hours. After reaction, the mixture was evaporated, and the residue was neutralized by sodium carbonate and poured into H2O. The precipitate was filtered by suction, washed was H2O and dried in vacuo to give 4.1 g of poly(p-tert-butoxystyrene/p-hydroxystyrene) as a white powder having Mw 10000 (GPC with polystyrene calibration). 1HNMR analysis indicated that 50% of p-hydroxy group was converted into p-tert-butoxy group.

Workup

  1. stirringstirring
  2. waitwas continued at room temperature for 22 hours
  3. customAfter reaction
  4. customthe mixture was evaporated
  5. additionpoured into H2O
  6. filtrationThe precipitate was filtered by suction
  7. washwashed
  8. customdried in vacuo

Sources & evidence

ORD record
ord-9fcb89fefbcb43e5a7b3f17879fc26ad
Source dataset
uspto-grants-1997_09
Patent number
US05670299

Reaction notes

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