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Azobisisobutyronitrile → Hydroxynaphthalene Methacrylate

HRID 350593
ノート
印刷プレビュー

反応式

HRID 350593 の反応式
[C:1]([O:6][C:7]1[C:16]2[C:11](=[C:12](O)[CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1)(=[O:5])[C:2]([CH3:4])=[CH2:3].C(OC(C(F)(F)F)C(F)(F)F)(=O)C(C)=C.C(C1CCOC1=O)(=O)C(C)=C.N(C(C)(C)C#N)=NC(C)(C)C#N>CCCCCC.C(OC(=O)C)C.O1CCCC1>[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].[OH:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 6547AzobisisobutyronitrileHCID 764691,1,1,3,3,3-Hexafluoro-2-propyl methacrylateHCID 219037765-Hydroxy-1-naphthalenyl methacrylateHCID 224927382-Methacryloyl-gamma-butyrolactone

生成物 1

HCID 67312192Hydroxynaphthalene Methacrylate収率 90%

試薬・触媒・溶媒 3

HCID 8028
Tetrahydrofuran
溶媒
HCID 8058Hexane溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

5-hydroxy-1-naphthalenyl methacrylate (a.k.a. hydroxynaphthalene methacrylate or NAMA) monomer (2.60 g, 0.0045 mole), hexafluoroisopropyl methacrylate (iPrHFAMA) monomer (23.20 g, 0.0800 mole), 2-methacryloyl-gamma-butyrolactone (a.k.a. gamma-butyrolactone methacrylate or GBLMA) monomer (3.88 g, 0.0051 mole), azobisisobutyronitrile (AlBN) (0.91 g, 10% the total mole of all monomers), 150 g of tetrahydrofuran (THF) and 72 g of ethylacetate were added to a 250 ml 3-neck round bottom flask equipped with condenser, thermometer, nitrogen inlet and magnetic stirrer bar. The reaction mixture was stirred at room temperature and bubbled with N2 flow for 45 minutes after which is was heated to 67–70° C. and stirred for 14 hours with a blanket N2 flow. After reaction, the solution was then cooled to room temperature and added dropwise to 1200 g of hexane. The resulting slurry was stirred for two hours before filtration. Solid was air dried on the Buckner filter for 1.5 hours, dissolved in acetone (15% wt-wt) and reprecipitated in 1200 g of hexane. The slurry was again stirred for two hours before filtration. The solid was collected and air dried for 2–3 hours before final drying in a vacuum oven at 60° C. overnight. Yield: 90%.

後処理

  1. customequipped with condenser
  2. custombubbled with N2 flow for 45 minutes after which
  3. temperatureis was heated to 67–70° C.
  4. stirringstirred for 14 hours with a blanket N2 flow
  5. customAfter reaction
  6. temperaturethe solution was then cooled to room temperature
  7. stirringThe resulting slurry was stirred for two hours before filtration
  8. customdried on the Buckner
  9. filtrationfilter for 1.5 hours
  10. dissolutiondissolved in acetone (15% wt-wt)
  11. customreprecipitated in 1200 g of hexane
  12. stirringThe slurry was again stirred for two hours before filtration
  13. customThe solid was collected
  14. customair dried for 2–3 hours
  15. custombefore final drying in a vacuum oven at 60° C. overnight

出典と根拠

ORDレコード
ord-4b1a085b588e46ee9c9cb2242aa40b39
出典データセット
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07183036B2

反応ノート

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