p-Toluenesulfonic acid → HCID 131724697, compound

HRID 1759677Notes

Reaction equation

HRID 1759677 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(OC1CCCCC1)=CC.[CH:31]1([O:37][CH2:38][CH2:39][CH2:40][O:41][C:42]2[CH:49]=[CH:48][C:45]([CH:46]=[CH2:47])=[CH:44][CH:43]=2)[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1.OC1C=CC(C=C)=CC=1>O1CCCC1>[CH:31]1([O:37][CH2:38][CH2:39][CH2:40][O:41][C:42]2[CH:43]=[CH:44][C:45]([CH:46]=[CH2:47])=[CH:48][CH:49]=2)[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]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 57003684HCID 57003684, compoundHCID 57104452HCID 57104452, compound

Product 1

HCID 131724697HCID 131724697, 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., 4.2 g (0.030 mol) of cyclohexyl 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 12.0 g. On 1H-NMR analysis, the ratio of p-(cyclohexyloxypropyl)oxystyrene units to p-hydroxystyrene units was approximately 23.0:77.0.

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 12.0 g

Sources & evidence

ORD record
ord-ee1f76a3deda475695b0e2e183c12198
Source dataset
uspto-grants-2005_01
Patent number
US06838224B2

Reaction notes

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