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Potassium acrylate → 1-Acryloyloxyethyl 4-acryloyloxybutyl carbonate

HRID 260624
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 260624
[C:1](=[O:16])([O:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12](=[O:15])[CH:13]=[CH2:14])[O:2][CH:3](Cl)[CH3:4].[C:17]([O-:21])(=[O:20])[CH:18]=[CH2:19].[K+]>CN(C)C=O.C1OCCOCCOCCOCCOCCOC1>[C:1](=[O:16])([O:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12](=[O:15])[CH:13]=[CH2:14])[O:2][CH:3]([O:21][C:17](=[O:20])[CH:18]=[CH2:19])[CH3:4]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 4429391Potassium acrylateHCID 539130511-Chloroethyl 4-acryloyloxybutyl carbonate

Produkt 1

HCID 539614401-Acryloyloxyethyl 4-acryloyloxybutyl carbonateAusbeute 89,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2855718-Crown-6KatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1-Chloroethyl 4-acryloyloxybutyl carbonate (1.253 g, 5.00 mmol) prepared as described in Preparation 10 is added to a suspension of freeze dried potassium acrylate (0.606 g, 5.50 mmol) and 18-crown-6 (0.066 g, 0.25 mmol) in dimethylformamide (50 ml) under a dry N2 atmosphere. After 5 days at 20° C. the solvent is removed under reduced pressure and the residue dissolved by adding dichloromethane (60 ml) and water (30 ml). After separating the phases the aqueous layer is extracted with dichloromethane (3×30 ml) and the combined organic phase washed with saturated aqueous sodium hydrogen carbonate (50 ml). The organic phase is dried (MgSO4) and the solvent removed under reduced pressure to give 1.28 g (89%) of the title product. 1H NMR (60 MHz, CDCl3): δ 1.58 (3 H, d, J=5 Hz, CH3 --CH), 1.80 (4 H, m, CH2 --CH2), 4.24 (4 H, m, 2×CH2 --O), 5.7-6.7 (6 H, m, 2×CH=CH2), 6.87 (1 H, k, J=5 Hz, CH--CH3).

Aufarbeitung

  1. customas described in Preparation 10
  2. customAfter 5 days at 20° C. the solvent is removed under reduced pressure
  3. dissolutionthe residue dissolved
  4. additionby adding dichloromethane (60 ml) and water (30 ml)
  5. customAfter separating the phases the aqueous layer
  6. extractionis extracted with dichloromethane (3×30 ml)
  7. washthe combined organic phase washed with saturated aqueous sodium hydrogen carbonate (50 ml)
  8. dry with materialThe organic phase is dried (MgSO4)
  9. customthe solvent removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-99da5765368d4b06ab6b4726afc49c5b
Quelldatensatz
uspto-grants-1996_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05529766

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