Styrene → Styrene

HRID 1460883Notes

Reaction equation

HRID 1460883 reaction equation
[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:9]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:15])/[CH:10]=[CH:11]\[C:12]([OH:14])=[O:13].[O:24]1[CH:29]=[CH:28][CH2:27][CH2:26][CH2:25]1.Cl.N1C=CC=CC=1>C1COCC1>[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:9]([O:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)(=[O:15])/[CH:10]=[CH:11]\[C:12]([O-:14])=[O:13].[C:9]([O:16][CH:29]1[CH2:28][CH2:27][CH2:26][CH2:25][O:24]1)(=[O:15])/[CH:10]=[CH:11]\[C:12]([O-:14])=[O:13]

Participants

8

Reactant 4

HCID 7501StyreneHCID 80803,4-dihydro-2H-pyranHCID 69130101-(Phenylmethyl) (2Z)-2-butenedioateHCID 10176127Pyridinium chloride

Product 3

HCID 7501StyreneHCID 58012570HCID 58012570, compoundHCID 86745284HCID 86745284, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Poly(styrene [50 mol %], benzyl hydrogen maleate [50 mol %]) was prepared by stirring at reflux for 25 hours a mixture of poly(styrene [50 mol %], maleic anhydride [50 mol %]), 200 mL of benzyl alcohol and 400 mL of THF. The THF was removed on a rotary evaporator, and the product was precipitated in hexane followed by precipitation from THF with diethyl ether to give 46 g of poly(styrene, benzyl hydrogen maleate). A mixture of 25 g of poly(styrene, benzyl hydrogen maleate), 150 mL of 3,4-dihydro-2H-pyran, and 0.5 g of pyridine hydrochloride was stirred at reflux 18 hours. THF was added to reduce the viscosity, and the mixture was stirred 1 hour with crosslinked poly(dimethylaminomethylstyrene). After filtration, the product was precipitated from the filtrate in methanol to give 29 g of poly(styrene, benzyl maleate, tetrahydropyranyl maleate). 1H HMR (360 MHz) shows the molar ratio of tetrahydropyranyl groups (δ 5.8 ppm) to benzyloxy groups (δ 5.0 ppm) to be about 4.4:1. Titration with 0.1N sodium hydroxide shows 0.09 meq/g of COOH groups. DSC: decomposition endotherm 140.75° C. TGA: 24.7% weight loss at 147.9° C.

Workup

  1. temperatureat reflux 18 hours
  2. filtrationAfter filtration
  3. customthe product was precipitated from the filtrate in methanol

Sources & evidence

ORD record
ord-6fbea4d712c24e9685ebcdeeeb7ed751
Source dataset
uspto-grants-1991_12
Patent number
US05072029

Reaction notes

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