Acrylic Acid → 1,3-Bis(4-benzoyl-3-hydroxyphenoxy)-2-propyl acrylate

HRID 621661

Reaktionsgleichung

Reaktionsgleichung von HRID 621661
FC(F)(F)S(O)(=O)=O.[C:9]([C:17]1[CH:43]=[CH:42][C:20]([O:21][CH2:22][CH:23]([OH:41])[CH2:24][O:25][C:26]2[CH:31]=[CH:30][C:29]([C:32](=[O:39])[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[C:28]([OH:40])[CH:27]=2)=[CH:19][C:18]=1[OH:44])(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:45](O)(=[O:48])[CH:46]=[CH2:47]>C1(C)C=CC=CC=1.C1(C=CC(O)=CC=1)O.COC1C=CC(O)=CC=1>[C:45]([O:41][CH:23]([CH2:22][O:21][C:20]1[CH:42]=[CH:43][C:17]([C:9](=[O:16])[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[C:18]([OH:44])[CH:19]=1)[CH2:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([C:32](=[O:39])[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[C:28]([OH:40])[CH:27]=1)(=[O:48])[CH:46]=[CH2:47]

Komponenten

7

Edukt 3

HCID 6581Acrylic AcidHCID 62406Trifluoromethanesulfonic acidHCID 12422352,2''-Dihydroxy-4,4''-(2-hydroxy-propane-1,3-diyldioxy)dibenzophenone

Produkt 1

HCID 136432701,3-Bis(4-benzoyl-3-hydroxyphenoxy)-2-propyl acrylateAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 785HydroquinoneKatalysatorHCID 90154-MethoxyphenolKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

3 g of trifluoromethanesulfonic acid, 0.1 g of hydroquinone and 0.1 g of hydroquinone monomethyl ether were added to a solution of 48.5 g (0.1 mole) of 1,3-bis-(4-benzoyl-3-hydroxyphenoxy)-2-propanol and 43.6 g (0.6 mole) of acrylic acid in 600 ml of toluene, and the solution was heated for 3 hours at a temperature of 105° to 110° C. After cooling to room temperature, the reaction mixture was washed with 1.5 liters of water. The toluene was then distilled off from the reaction mixture under a pressure of 20 mbar. The oily residue remaining was dissolved in hot ethanol. Cooling this solution to room temperature gave 40 g (75 percent of theory) of 1,3-bis-(4-benzoyl-3-hydroxyphenoxy)-prop-2-yl acrylate in the form of colorless crystals having a melting point of 98° to 100° C. and a purity of 99 percent (HPLC). The UV spectrum gave two absorption maxima at wave lengths of 287 nm (extinction 0.520; extinction coefficient 28,100) and 324 nm (extinction 0.335; extinction coefficient 18,100).

Aufarbeitung

  1. temperaturethe solution was heated for 3 hours at a temperature of 105° to 110° C
  2. washthe reaction mixture was washed with 1.5 liters of water
  3. distillationThe toluene was then distilled off from the reaction mixture under a pressure of 20 mbar
  4. dissolutionThe oily residue remaining was dissolved in hot ethanol
  5. temperatureCooling this solution to room temperature

Quellen und Nachweise

ORD-Eintrag
ord-449ceddab78d44f5946e5b79281c34b4
Quelldatensatz
uspto-grants-1989_04
Patentnummer
US04824892

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