Acetic Acid → 2-ethyl-2-adamantyl Methacrylate p-hydroxystyrene

HRID 2306526Notes

Reaction equation

HRID 2306526 reaction equation
[C:1]([O:6][C:7]1([CH2:17][CH3:18])[CH:14]2[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:16][CH:8]1[CH2:9]3)[CH2:13]2)(=[O:5])[C:2]([CH3:4])=[CH2:3].C([O:22][C:23]1[CH:30]=[CH:29][C:26]([CH:27]=[CH2:28])=[CH:25][CH:24]=1)(=O)C.CO.C(O)(=O)C>CN(C)C1C=CN=CC=1.O>[C:1]([O:6][C:7]1([CH2:17][CH3:18])[CH:8]2[CH2:16][CH:12]3[CH2:11][CH:10]([CH2:15][CH:14]1[CH2:13]3)[CH2:9]2)(=[O:5])[C:2]([CH3:4])=[CH2:3].[OH:22][C:23]1[CH:30]=[CH:29][C:26]([CH:27]=[CH2:28])=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 758214-Ethenylphenyl acetateHCID 98136452-Ethyl-2-methacryloyloxyadamantane

Product 1

HCID 225083922-ethyl-2-adamantyl Methacrylate p-hydroxystyrene

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

Into a flask were charged 250 g of the copolymer of 2-ethyl-2-adamantyl methacrylate and p-acetoxystyrene (20:80) obtained in Synthesis Example 4, 10.4 g (0.084 mol) of 4-dimethylaminopyridine and 202 g of methanol, and aged for 20 hours under reflux. After cooling, the reaction liquid was neutralized with 7.6 g (0.126 mol) of glacial acetic acid and poured into a large amount of water to precipitate a polymer. The deposited polymer was filtrated, dissolved in acetone, then, poured into a large amount of water to cause precipitation, and this operation was repeated three times in total for purification.

Workup

  1. temperatureunder reflux
  2. temperatureAfter cooling
  3. customthe reaction liquid
  4. customto precipitate a polymer
  5. filtrationThe deposited polymer was filtrated
  6. dissolutiondissolved in acetone
  7. additionpoured into a large amount of water
  8. customprecipitation
  9. customtotal for purification

Sources & evidence

ORD record
ord-2db065eb04064f0e83e45ff1399c260f
Source dataset
uspto-grants-2004_12
Patent number
US06828079B2

Reaction notes

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