Methacrylonitrile → 2-Methyladamantanyl methacrylate methacrylonitrile alpha-butyrolactone Methacrylate

HRID 2120518Notes

Reaction equation

HRID 2120518 reaction equation
[C:1]([O:6][C:7]12[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][CH:9]([CH2:10]3)[CH:8]1[CH3:17])[CH2:14]2)(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:18](#[N:22])[C:19]([CH3:21])=[CH2:20].[C:23]([OH:28])(=[O:27])[C:24]([CH3:26])=[CH2:25].[C:29]1(=[O:34])[O:33][CH:30]1[CH2:31][CH3:32].CCC(N=NC(C#N)(CC)C)(C#N)C>O1CCCC1>[C:1]([O:6][C:7]12[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][CH:9]([CH2:10]3)[CH:8]1[CH3:17])[CH2:14]2)(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:18](#[N:22])[C:19]([CH3:21])=[CH2:20].[C:23]([OH:28])(=[O:27])[C:24]([CH3:26])=[CH2:25].[C:29]1(=[O:34])[O:33][CH:30]1[CH2:31][CH3:32]

Participants

6

Reactant 4

HCID 31368MethacrylonitrileHCID 930792,2'-Azobis(2-methylbutyronitrile)HCID 21983218alpha-Butyrolactone MethacrylateHCID 219832202-Methyladamantanyl methacrylate

Product 1

HCID 867593492-Methyladamantanyl methacrylate methacrylonitrile alpha-butyrolactone Methacrylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
90 °C

Procedure

2-Methyladamantanyl methacrylate (14.21 g, 0.061 mol), methacrylonitrile (3.05 g, 0.045 mol), and alpha-butyrolactone methacrylate (7.74 g, 0.045 mol) were dissolved in 66 mL of tetrahydrofuran. The resulting colorless solution was deoxygenated by gently bubbling a stream of N2 through the stirring solution for 15 minutes, placed under N2, and heated to 90° C. (oil bath temperature). VAZO67 (0.58 g, 0.0030 mol) dissolved in 7 ml of tetrahydrofuran, was then added to the refluxing mixture over 10 minutes. The polymerization was then refluxed with stirring for 20 hours and cooled to room temperature. The polymer was isolated by precipitation into 800 mL of hexanes, filtered, dried, re-dissolved in 70 mL of tetrahydrofuran, precipitated into 800 mL of hexanes, filtered, washed well with hexanes, and dried in a vacuum oven at 40° C. for 24 hours. Yield 19.8 g (79% of theory). Composition of the title terpolymer was determined by quantitative C-13 NMR and was found to be within experimental error of the monomer feed ratio.

Workup

  1. customThe resulting colorless solution was deoxygenated
  2. customby gently bubbling a stream of N2 through the stirring solution for 15 minutes
  3. additionwas then added to the refluxing mixture over 10 minutes
  4. temperatureThe polymerization was then refluxed
  5. temperaturecooled to room temperature
  6. filtrationfiltered
  7. customdried
  8. dissolutionre-dissolved in 70 mL of tetrahydrofuran
  9. customprecipitated into 800 mL of hexanes
  10. filtrationfiltered
  11. washwashed well with hexanes
  12. customdried in a vacuum oven at 40° C. for 24 hours

Sources & evidence

ORD record
ord-cb8f30e699b246d8821a4482678fbe34
Source dataset
uspto-grants-2004_02
Patent number
US06692888B1

Reaction notes

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