p-(1-Ethoxyethoxy)styrene → HCID 69084924, compound

HRID 1784325Notes

Reaction equation

HRID 1784325 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH:12]([O:14][CH2:15][CH3:16])[CH3:13])[CH:6]=[CH2:7].C(OC(OC1C=CC(C=C)=CC=1)C)C>O1CCCC1.CO.CC(C)=O.C([Li])CCC>[CH2:15]([O:14][CH:12]([O:11][C:10]1[CH:3]=[CH:4][C:5]([CH:6]=[CH2:7])=[CH:8][CH:9]=1)[CH3:13])[CH3:16].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH:12]([O:14][CH2:15][CH3:16])[CH3:13])[CH:6]=[CH2:7]

Participants

7

Reactant 2

HCID 9855712p-(1-Ethoxyethoxy)styreneHCID 23084984HCID 23084984, compound

Product 1

HCID 69084924HCID 69084924, compoundYield 148%

Reagents, catalysts & solvents 4

HCID 178418339ButyllithiumCatalystHCID 180AcetoneSolventHCID 887MethanolSolvent3×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

In a reaction vessel, 111.2 g (0.5 mol) of 3-methoxy-4-(1-ethoxyethoxy)styrene purified by distillation and 96.1 g (0.5 mol) of 4-(1-ethoxyethoxy)styrene (produced by Tosoh Corp.) were dissolved in 500 ml of dehydrated tetrahydrofuran. While stirring the resulting solution, a nitrogen gas was passed into the system and after cooling the system to −78° C., 0.02 mol of n-butyl lithium was added thereto and the polymerization was initiated. The polymerization degree was confirmed by sampling a part of the reaction solution every 30 minutes. When a desired polymerization degree was achieved, the polymerization was stopped by adding methanol to the reaction solution. After waiting until the reaction solution was cooled to room temperature, the reaction solution was added dropwise in 5 L of methanol to precipitate a polymer. The solid obtained by filtration was dissolved in 300 ml of acetone and again added dropwise in 5 L of methanol and after filtration, the solid obtained was dried under reduced pressure to obtain 153.4 g of a [3-methoxy-4-(1-ethoxyethoxy)styrene]-[4-(1-ethoxyethoxy)styrene] copolymer.

Workup

  1. aliquotby sampling a part of the reaction solution every 30 minutes
  2. customWhen a desired polymerization degree
  3. waitAfter waiting until the reaction solution
  4. temperaturewas cooled to room temperature
  5. customto precipitate a polymer
  6. customThe solid obtained by filtration
  7. filtrationafter filtration
  8. customthe solid obtained
  9. customwas dried under reduced pressure

Sources & evidence

ORD record
ord-2978a0369c104991a56a0422e78377f2
Source dataset
uspto-grants-2009_03
Patent number
US07504193B2

Reaction notes

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