Phenol → Methyl 4-(phenoxymethyl)benzoate

HRID 1500988Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1500988
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.[C:13]1([OH:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[O:19]([CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

5

Edukt 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 256687Methyl 4-(bromomethyl)benzoate

Produkt 1

HCID 925826Methyl 4-(phenoxymethyl)benzoateAusbeute 103,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of methyl 4-(bromomethyl)benzoate (1000 mg, 4.37 mmol), phenol (493 mg, 5.24 mmol), potassium carbonate (1200 mg, 8.73 mmol) and acetone (20 mL) was stirred at 60° C. under nitrogen atmosphere for 4 hours. The resultant mixture was concentrated to give a residue. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=4:1) to give methyl 4-(phenoxymethyl)benzoate as a white solid (1100 mg, 100%). 1H NMR (300 MHz, CDCl3): δ 8.01 (d, J=8.1 Hz, 2H), 7.62 (d, J=8.1 Hz, 2H), 7.35-7.30 (m, 2H), 7.04 (d, J=7.8 Hz, 2H), 6.98 (t, J=7.2 Hz, 1H), 5.23 (s, 2H), 3.88 (s, 3H).

Aufarbeitung

  1. concentrationThe resultant mixture was concentrated
  2. customto give a residue
  3. customThe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=4:1)

Quellen und Nachweise

ORD-Eintrag
ord-6b705505afbd472dadedf86a8c558b01
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09206128B2

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