Toluene → Propanoic acid, 2-(4-hydroxyphenoxy)-, ethyl ester

HRID 485842Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 485842
C([C:3]1[CH:16]=[CH:15][C:6]([O:7][CH:8]([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:5][CH:4]=1)=O.C1(C)C=CC=CC=1.C(OO)(=[O:26])C>O>[OH:26][C:3]1[CH:16]=[CH:15][C:6]([O:7][CH:8]([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:5][CH:4]=1

Komponenten

5

Edukt 3

HCID 1140TolueneHCID 6585Peracetic AcidHCID 3016639Ethyl 2-(4-formylphenoxy)propionate

Produkt 1

HCID 3017597Propanoic acid, 2-(4-hydroxyphenoxy)-, ethyl esterAusbeute 77,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

While stirring a mixture of 22.5 g of ethyl 2-(4-formylphenoxy)propionate ([α]D25 =+51.5°) and 60 g of toluene at room temperature, 22.8 g of 40% peracetic acid was dropwise added. After stirring at 20° to 30° C. for 2 hours and at 50° C. for 2 hours, 0.2 g of water was added, and the mixture was stirred for 2 hours. After cooling the reaction mixture to room temperature, 40 g of water was added. The aqueous layer was separated. The organic layer was washed with 40 g of water, followed by washing twice with 40 g of a 5% sodium hydrogen carbonate aqueous solution, then with 40 g of a 5% sodium hydrogen sulfite aqueous solution and further with 40 g of water. Then, the reaction mixture was concentrated by distilling off toluene under reduced pressure, and subjected to distillation under reduced pressure, whereby 16.5 g of (+)-ethyl 2-(4-hydroxyphenoxy)propionate was obtained as a colorless transparent liquid. The boiling point was from 130° to 140° C./1 mmHg.

Aufarbeitung

  1. stirringAfter stirring at 20° to 30° C. for 2 hours and at 50° C. for 2 hours
  2. stirringthe mixture was stirred for 2 hours
  3. customThe aqueous layer was separated
  4. washThe organic layer was washed with 40 g of water
  5. washby washing twice with 40 g of a 5% sodium hydrogen carbonate aqueous solution
  6. concentrationThen, the reaction mixture was concentrated
  7. distillationby distilling off toluene under reduced pressure
  8. distillationsubjected to distillation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-17c524894ba64fb689f706dc73d851be
Quelldatensatz
uspto-grants-1985_08
Patentnummer
US04537984

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