p-Toluenesulfonic acid → HCID 69079143, compound

HRID 1594952Notes

Reaction equation

HRID 1594952 reaction equation
C(OC(C)COC)(=O)C.[CH:10]#[C:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH:30]([N:32]1[CH2:36][CH2:35][CH2:34][C:33]1=[O:37])=[CH2:31]>C(C(C)=O)C(C)C>[OH:18][C:15]1[CH:16]=[CH:17][C:12]([CH:11]=[CH2:10])=[CH:13][CH:14]=1.[O:37]=[C:33]1[CH2:34][CH2:35][CH2:36][N:32]1[CH:30]([O:18][C:15]1[CH:16]=[CH:17][C:12]([CH:11]=[CH2:10])=[CH:13][CH:14]=1)[CH3:31]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 6917N-vinyl-2-pyrrolidoneHCID 7946Propylene glycol methyl ether acetateHCID 327584-Ethynylphenol

Product 1

HCID 69079143HCID 69079143, compound

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

Into 200 parts of propylene glycol monomethyl ether acetate was dissolved 50.0 parts of poly(p-vinylphenol) [“VP-2500”, manufactured by Nippon Soda, having a weight average molecular weight of 4,000 and a distribution of 1.15]. The solution was cooled to room temperature and a catalytic amount of p-toluenesulfonic acid was added thereto and dissolved. To this solution was added dropwise 4.63 parts of N-vinyl-2-pyrrolidone over 30 minutes. Then the solution was kept at room temperature for 2 hours. After adding methyl isobutyl ketone, the solution was washed with ion-exchanged water. The organic layer after washing was concentrated to 250 parts, combined with 250 parts of propylene glycol monomethyl ether acetate and further concentrated to 124 parts. The solid content of the concentrate measured by weight-loss on heating was 39.65% by weight. A broad peak at 6.0 ppm was confirmed by 1H-NMR [270 MHz, in (dimethylsulfoxide)-d6] and assigned to the methine proton in —O—CH(CH3)—N<. From the ratio of integrated area for this methine proton and that for the aromatic protons, it was confirmed that the resin was a copolymer constituted by p-hydroxystyrene unit and p-[1-(2-oxo-1-pyrrolidinyl)ethoxy]styrene in a ratio of 91:9. The resin was referred to as Resin R1.

Workup

  1. dissolutiondissolved
  2. washthe solution was washed with ion-exchanged water
  3. washThe organic layer after washing
  4. concentrationwas concentrated to 250 parts
  5. concentrationfurther concentrated to 124 parts
  6. temperatureon heating

Sources & evidence

ORD record
ord-f861dd168e3d4b199aadc82af2e104a1
Source dataset
uspto-grants-2001_09
Patent number
US06284863B1

Reaction notes

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