Pyridine → HCID 131724431, compound

HRID 1581906Notes

Reaction equation

HRID 1581906 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH2:7])=[CH:4][CH:3]=1.N1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:16]([O:19][C:20](=O)[CH3:21])(=O)[CH3:17].[C:23]([O:26][CH2:27][CH3:28])(=[O:25])[CH3:24]>C(OC(C)COC)(=O)C>[CH:11]1([CH2:17][CH2:16][O:19][CH:20]([O:1][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[CH2:7])=[CH:4][CH:3]=2)[CH3:21])[CH2:23][CH2:15][CH2:14][CH2:13][CH2:12]1.[C:23]([O:26][C:27]1[CH:3]=[CH:4][C:5]([CH:6]=[CH2:7])=[CH:8][CH:28]=1)(=[O:25])[CH3:24].[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH2:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 624534-Vinylphenol

Product 1

HCID 131724431HCID 131724431, compound

Reagents, catalysts & solvents 1

HCID 7946Propylene glycol methyl ether acetateSolvent

Conditions

Temperature
20 °C

Procedure

p-Hydroxystyrene (70 g) (VP-8000, manufactured by Nippon Soda Co., Ltd.) was dissolved in 320 g of propylene glycol monomethyl ether acetate (PGMEA) by heating, after dehydration by distillation under reduced pressure, the solution was cooled to 20° C. To the solution were added 0.35 g of pyridinium p-toluenesulfonate and 22.4 g of cyclohexane ethanol. t-Butyl vinyl ether (17.5 g) was gradually added to the solution to perform reaction at 20° C. for 5 hours. To the reaction solution were added 5.53 g of pyridine, and then 5.9 g of acetic anhydride was gradually added. The solution was subjected to reaction at room temperature for 1 hour. Ethyl acetate (320 ml) was added to the solution, and the reaction solution was washed with 150 ml of distilled water three times. The solvent was distilled off and the solution was concentrated. The thus-obtained oil was dissolved in 100 ml of acetone, and the solution was gradually poured into 2 liters of distilled water. The precipitated powder was filtered and dried, thereby 58 g of resin A-38 was obtained.

Workup

  1. temperatureby heating
  2. distillationafter dehydration by distillation under reduced pressure
  3. additionTo the solution were added 0.35 g of pyridinium p-toluenesulfonate and 22.4 g of cyclohexane ethanol
  4. additiont-Butyl vinyl ether (17.5 g) was gradually added to the solution
  5. customreaction at 20° C. for 5 hours
  6. customThe solution was subjected to reaction at room temperature for 1 hour
  7. washthe reaction solution was washed with 150 ml of distilled water three times
  8. distillationThe solvent was distilled off
  9. concentrationthe solution was concentrated
  10. dissolutionThe thus-obtained oil was dissolved in 100 ml of acetone
  11. additionthe solution was gradually poured into 2 liters of distilled water
  12. filtrationThe precipitated powder was filtered
  13. customdried
  14. customwas obtained

Sources & evidence

ORD record
ord-d4232695fbed45bab35315bdb057905d
Source dataset
uspto-grants-2004_05
Patent number
US06733951B2

Reaction notes

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