Water → Ethyl 2-(benzyloxy)benzoate

HRID 38639

Reaktionsgleichung

Reaktionsgleichung von HRID 38639
[OH:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].C([O-])([O-])=O.[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>CC#N>[CH2:19]([O:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 7498Benzyl BromideHCID 8365Ethyl SalicylateHCID 11430Potassium Carbonate

Produkt 1

HCID 345928Ethyl 2-(benzyloxy)benzoateAusbeute 94,71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 68 (5.8 g, 34.9 mmol) in CH3CN (150 ml) was added K2CO3 (10.6 g, 76.8 mmol). The mixture was added benzyl bromide (6.57 g, 38.39 mmol) and refluxed for 8 h under N2 atmosphere. The reaction mixture was cooled to 25° and poured into H2O (500 ml), and then extracted with CH2Cl2. The organic layer was washed with H2O, dried over MgSO4 and evaporated. The crude products were purified by distillation to give 73 as colorless liquid. (8.5 g, 33.2 mmol). Yield: 94.71%; MS (EI, 70 eV): m/z 256.3 (M+); 1H-NMR (CDCl3, 200 MHz): δ 1.33=(t, J=7.2 Hz, 3H), 4.35 (q, =7.2, 7.0 Hz, 2H), 5.15 (s, 2H), 7.00 (d, =8.0 Hz, 2H), 7.32-7.45 (m, 5H), 7.49 (d, J=8.2 Hz, 1H), 7.82 (dd, J=8.2, 1.8 Hz, 1H); 13C-NMR (CDCl3, 50 MHz) δ: 166.60, 158.01, 136.77, 133.25, 131.69, 128.49, 127.80, 126.99, 121.20, 120.56, 113.75, 70.57, 60.93, 14.29; Anal. Calcd for C16H16O3: C, 74.98; H, 6.29.

Aufarbeitung

  1. temperaturerefluxed for 8 h under N2 atmosphere
  2. temperatureThe reaction mixture was cooled to 25°
  3. extractionextracted with CH2Cl2
  4. washThe organic layer was washed with H2O
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. distillationThe crude products were purified by distillation

Quellen und Nachweise

ORD-Eintrag
ord-eb760ee673ac4bd98bb759caad1f3ae1
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524740B2

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