Desoxyanisoin → 1,2-Bis(4-hydroxyphenyl)ethanone

HRID 525635

Reaktionsgleichung

Reaktionsgleichung von HRID 525635
[C:1]1([C:9]([CH2:11][C:12]2[CH:19]=[CH:18][C:15]([O:16]C)=[CH:14][CH:13]=2)=[O:10])[CH:8]=[CH:7][C:4]([O:5]C)=[CH:3][CH:2]=1.Cl.N1C=CC=CC=1>O>[OH:5][C:4]1[CH:7]=[CH:8][C:1]([C:9]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([OH:16])=[CH:18][CH:19]=2)=[O:10])=[CH:2][CH:3]=1

Komponenten

4

Edukt 2

HCID 67120Desoxyanisoin2×HCID 10176127Pyridinium chloride

Produkt 1

HCID 134272011,2-Bis(4-hydroxyphenyl)ethanoneAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
200 °C

Versuchsvorschrift

4,4′-Bishydroxydeoxybenzoin (BHDB) was prepared by demethylation of desoxyanisoin, according to the literature. (See, Ellzey et al. Macromolecules 2006; 39: 3553-3558; Ranganathan et al. Macromolecules 2006; 39: 5974-5975.) Desoxyanisoin (50 g, 195.1 mmol) and pyridine hydrochloride (90.2 g, 780.5 mmol) were added to a round-bottom flask equipped with a condenser. The mixture was refluxed for 5 h at 200° C., cooled to room temperature, and poured into water. The precipitate was filtered and recrystallized from acetic acid to give 38 g (85% yield) of the desired product. 1H-NMR (DMSO-d6, ppm): 10.35 (s, 1H, HO—Ar—CO), 9.28 (s, 1H, HO—Ar—CH2), 7.91 (d, 2H, Ar—H), 7.05 (d, 2H, Ar—H), 6.84 (d, 2H, Ar—H), 6.68 (d, 2H, Ar—H), 4.09 (s, 2H, Ar—CO—CH7—Ar)

Aufarbeitung

  1. customequipped with a condenser
  2. temperaturecooled to room temperature
  3. filtrationThe precipitate was filtered
  4. customrecrystallized from acetic acid

Quellen und Nachweise

ORD-Eintrag
ord-b31471e133254bedb74ef766a72a1387
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09340635B2

Verknüpfte Notizen

Wird geladen…