Water → 4-Benzyloxybenzophenone

HRID 1261384

Reaktionsgleichung

Reaktionsgleichung von HRID 1261384
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:11])=[CH:6][CH:5]=1.[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CN(C=O)C>[CH2:18]([O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:11])=[CH:8][CH:9]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 7498Benzyl BromideHCID 143474-HydroxybenzophenoneHCID 24758Sodium hydride

Produkt 1

HCID 4581934-Benzyloxybenzophenone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

NaH (60% in mineral oil, 1.2 g, 30 mmol) was added to an ice-cooled solution of (4-hydroxy-phenyl)-phenyl-methanone (5 g, 25.2 mmol) in DMF (25 mL). The resulting mixture was stirred for 20 minutes at room temperature (r.t.). Benzyl bromide (6.1 mL, 50 mmol) was added at 0° C. The reaction temperature was raised to r.t. after 1 h and thereafter stirred for additional 2 h. Water (20 mL) was added and the aqueous phase was extracted with dichloromethane (2×30 mL). The combined organic phase was concentrated and purified by flash chromatography (eluent: 100% dichloromethane). Yield: 7.0 g, 96% of 1. 1H NMR (400 MHz, CDCl3): δ 7.83 (d, J=8.4 Hz, 2H), 7.77 (d, J=7.2 Hz, 2H), 7.58-7.52 (m, 1H), 7.50-7.32 (m, 7H), 7.03 (d, J=8.4 Hz, 2H), 5.17 (s, 2H).

Aufarbeitung

  1. temperatureThe reaction temperature was raised to r.t. after 1 h
  2. stirringstirred for additional 2 h
  3. extractionthe aqueous phase was extracted with dichloromethane (2×30 mL)
  4. concentrationThe combined organic phase was concentrated
  5. custompurified by flash chromatography (eluent: 100% dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-d91a4993e5184457836fef0b7698d08f
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08470872B2

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