Water → 4-(4-acryloxybutoxy)benzoic acid

HRID 2229989

Reaktionsgleichung

Reaktionsgleichung von HRID 2229989
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1.[C:16](O)(=[O:19])[CH:17]=[CH2:18].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>ClC(Cl)(Cl)C.C(C1CC(=CN(C)C)C=C(C(C)(C)C)C=1O)(C)(C)C>[C:16]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1)(=[O:19])[CH:17]=[CH2:18]

Komponenten

7

Edukt 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 6581Acrylic AcidHCID 152185964-(4-Hydroxybutoxy)benzoic acid

Produkt 1

HCID 110327354-(4-acryloxybutoxy)benzoic acidAusbeute 63,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 867583672,6 Di-tert-butyl-4-(dimethylaminomethylene)phenolKatalysatorHCID 62781,1,1-TrichloroethaneLösungsmittel

Versuchsvorschrift

276.6 g of 4-chlorobutyl acetate (1.8 mol) were added to a solution of 249 g of ethyl 4-hydroxybenzoate (1.5 mol), 3 g of potassium iodide (0.018 mol) and 248 g of potassium carbonate (1.8 mol) in 2 l of DMF, and the mixture was stirred at 90° C. for 11 hours. The reaction mixture was poured into 5 l of ice-water, and the precipitate was filtered off with suction and washed with 4 l of ice-water. The crude product was dissolved in 3 l of ethanol, potassium hydroxide (400 g) was added, and the mixture was refluxed for 3 hours. The reaction mixture was poured into 6 l of ice-water and acidified using concentrated hydrochloric acid, and the precipitate was filtered off. The precipitate was washed with water until neutral and then dried, giving 282.1 g of 4-(4′-hydroxybutoxy)benzoic acid (yield 89%). b) A solution of 282 g of 4-(4′-hydroxybutoxy)benzoic acid (1.34 mol), 230 ml of freshly distilled acrylic acid (3.35 mol), 0.3 g of 2,6-di-tert-butyl-4-(dimethylaminomethylene)phenol (Ethanox® 703) and 23.7 g of p-toluenesulfonic acid in 1.1 liter of 1,1,1-trichloroethane was refluxed for 10 hours on a water separator. The reaction mixture was cooled to 60° C.-70° C. and stirred into 2.5 l of petroleum ether, and the precipitate was filtered off. After washing with petroleum ether, the precipitate was dried for 24 hours at room temperature under reduced pressure, giving 223.7 g of 4-(4′-acryloxybutoxy)benzoic acid (yield 60%).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to 60° C.-70° C.
  2. filtrationthe precipitate was filtered off
  3. washAfter washing with petroleum ether
  4. customthe precipitate was dried for 24 hours at room temperature under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-463e947aed9748888758c2904b920c0b
Quelldatensatz
uspto-grants-2002_07
Patentnummer
US06423246B1

Verknüpfte Notizen

Wird geladen…