p-Toluenesulfonic acid → HCID 131724323, compound

HRID 1840700Notes

Reaction equation

HRID 1840700 reaction equation
[CH:1]#[C:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC1C=CC=CC=1)=CC.[CH2:32]([O:39][CH:40]([O:43][C:44]1[CH:51]=[CH:50][C:47]([CH:48]=[CH2:49])=[CH:46][CH:45]=1)[CH2:41][CH3:42])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.OC1C=CC(C=C)=CC=1>O1CCCC1>[CH2:32]([O:39][CH:40]([O:43][C:44]1[CH:51]=[CH:50][C:47]([CH:48]=[CH2:49])=[CH:46][CH:45]=1)[CH2:41][CH3:42])[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1.[OH:9][C:6]1[CH:7]=[CH:8][C:3]([CH:2]=[CH2:1])=[CH:4][CH:5]=1

Participants

7

Reactant 5

HCID 6101p-Toluenesulfonic acidHCID 327584-EthynylphenolHCID 624534-VinylphenolHCID 23504263HCID 23504263, compoundHCID 54218220{[(Prop-1-en-1-yl)oxy]methyl}benzene

Product 1

HCID 131724323HCID 131724323, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 48 g of tetrahydrofuran was dissolved 12 g of poly(p-hydroxystyrene) having a weight average molecular weight (Mw) of 9,000 and a dispersity (Mw/Mn) of 1.05. A catalytic amount of p-toluenesulfonic acid was added. At 10° C., 4.3 g (0.029 mol) of benzyl propenyl ether was added to the solution, which was stirred for 2 hours. The reaction mixture was precipitated from a water/isopropanol mixture, followed by filtration and drying. The end polymer was obtained in an amount of 13.5 g. On 1H-NMR analysis, the ratio of p-(1-benzyloxypropyl)oxystyrene units to p-hydroxystyrene units was approximately 22.5:77.5.

Workup

  1. customThe reaction mixture was precipitated from a water/isopropanol mixture
  2. filtrationfollowed by filtration
  3. customdrying
  4. customThe end polymer was obtained in an amount of 13.5 g

Sources & evidence

ORD record
ord-4d38b308faf3456bac818294cccbc6c6
Source dataset
uspto-grants-2004_01
Patent number
US06682869B2

Reaction notes

Loading…