Styrene → HCID 86755459, compound

HRID 1421352Notes

Reaction equation

HRID 1421352 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1C=C)=[CH2:2].[CH:11]([S:19]([O-:22])(=[O:21])=[O:20])=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Na:23].C=CC1C=CC=CC=1.CC1(C)N([O])C(C)(C)CCC1.S(OOS([O-])(=O)=O)([O-])(=O)=O.[K+].[K+].S(=O)(O)[O-].[Na+]>O.C(O)CO>[CH2:2]=[CH:1][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:11]([S:19]([O-:22])(=[O:20])=[O:21])=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Na:23]

Participants

9

Reactant 6

HCID 7501StyreneHCID 24412Potassium PersulfateHCID 666661,2-Diethenylbenzene2×HCID 2724126TempoHCID 23665763Sodium BisulfiteHCID 86755460HCID 86755460, compound

Product 1

HCID 86755459HCID 86755459, compound

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

0.5 molar ratio of St:SS-Na:DVB To a round bottom flask is added styrenesulfonate-sodium salt (SS-Na, 10 g, 0.0487 mole), styrene (5.06g, 0.0487 mole), divinylbenzene (DVB, 3.17 g, 0.02435 mole), and TEMPO (0.53 g, 0.00341 mole). To this is added ethylene glycol (24 mL) and water (16 mL) and heated to 80° C. Then a redox initiator system, potassium persulfate (0.51 g, 0.00189 mole) and sodium bisulfite (0.25 g), is added. After 40 minutes, the heterogeneous solution is heated to reflux. After 7 hours, the reaction is cooled and precipitated into a solution of methanol/acetone (200 mL, 1:1 ratio).

Workup

  1. temperaturethe heterogeneous solution is heated to reflux
  2. waitAfter 7 hours
  3. temperaturethe reaction is cooled
  4. customprecipitated into a solution of methanol/acetone (200 mL, 1:1 ratio)

Sources & evidence

ORD record
ord-4bd180a0170741aca5c26d5c234967b8
Source dataset
uspto-grants-2000_06
Patent number
US06075105

Reaction notes

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