Ethanol → 2-Benzyloxybenzoic acid

HRID 38640

Reaktionsgleichung

Reaktionsgleichung von HRID 38640
[CH2:1]([O:8][C:9]1[CH:19]=[CH:18][CH:17]=[CH:16][C:10]=1[C:11]([O:13]CC)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].CCO>O>[CH2:1]([O:8][C:9]1[CH:19]=[CH:18][CH:17]=[CH:16][C:10]=1[C:11]([OH:13])=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 345928Ethyl 2-(benzyloxy)benzoate

Produkt 1

HCID 18105812-Benzyloxybenzoic acidAusbeute 84,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a suspension of 73 (4.0 g, 15.6 mmol) in H2O (150 ml) were added NaOH (3.1 g, 78.0 mmol) and EtOH (5 ml). The mixture was reflux for 12 h, and cooled to 25° C. The solid was filtered out and the filtrate was acidified with 2N HCl. The precipitate was collected and washed with H2O. The crude product was recrystallized from to give 78 as white solid. (3.0 g, 13.2 mmol). Yield: 84.6%; mp 73-75° C.; MS (EI, 70 eV): m/z 228.3 (M+); 1H-NMR (CDCl3, 200 MHz): δ 5.27 (s, 2H), 7.08-7.54 (m, 8H), 6.93 (dd, J=8.0, 1.8 Hz, 1H); 13C-NMR (CDCl3, 50 MHz) δ: 165.43, 157.40, 135.02, 134.34, 133.88, 129.16, 127.92, 122.44, 118.09, 113.11, 72.23; Anal. Calcd for C14H12O3: C, 73.67; H, 5.30.

Aufarbeitung

  1. temperatureThe mixture was reflux for 12 h
  2. filtrationThe solid was filtered out
  3. customThe precipitate was collected
  4. washwashed with H2O
  5. customThe crude product was recrystallized from

Quellen und Nachweise

ORD-Eintrag
ord-11b9b0ab40304925a3d101c2731ff662
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524740B2

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