Benzyl Alcohol → Styrene

HRID 1460882Notes

Reaction equation

HRID 1460882 reaction equation
[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:9]1(=[O:15])[O:14][C:12](=[O:13])[CH:11]=[CH:10]1.[CH2:16]([OH:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1COCC1>[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:12]([O:23][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:13])/[CH:11]=[CH:10]\[C:9]([OH:14])=[O:15]

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 7501StyreneHCID 7923Maleic Anhydride

Product 2

HCID 7501StyreneHCID 69130101-(Phenylmethyl) (2Z)-2-butenedioate

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. customPoly(styrene [50 mol %], benzyl hydrogen maleate [50 mol %]) was prepared
  2. temperatureat reflux for 25 hours
  3. customThe THF was removed on a rotary evaporator
  4. customthe product was precipitated in hexane
  5. customfollowed by precipitation from THF with diethyl ether

Sources & evidence

ORD record
ord-11042106ee9147c4913802efc3abf0bf
Source dataset
uspto-grants-1991_12
Patent number
US05072029

Reaction notes

Loading…