Potassium Carbonate → Methyl 3-{4-[(3-benzoylbenzyl)oxy]phenyl}propanoate

HRID 922173

Reaktionsgleichung

Reaktionsgleichung von HRID 922173
[CH3:1][O:2][C:3](=[O:13])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:21][C:22]1[CH:23]=[C:24]([C:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:29])[CH:25]=[CH:26][CH:27]=1>CN(C=O)C>[C:28]([C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][CH:25]=1)[CH2:21][O:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][C:3]([O:2][CH3:1])=[O:13])=[CH:7][CH:8]=1)(=[O:29])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl esterHCID 895863-(Bromomethyl)benzophenone

Produkt 1

HCID 66685586Methyl 3-{4-[(3-benzoylbenzyl)oxy]phenyl}propanoateAusbeute 83,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a 250 mL RB flask fitted with magnetic stirrer was charged 45 mL of DMF. To the stirred solvent was added 3-(4-Hydroxy-phenyl)-propanoic acid methyl ester (4.5 g, 16.35 mmol) followed by K2CO3 (6.78 g, 49.074 mmol) and the resulting mixture stirred at room temperature for 30 minutes. (3-bromomethyl-phenyl)-phenyl-methanone (2.94 g, 16.35 mmol) was added to the above mixture and stirring continued at RT for 24 h. After completion of the reaction (reaction monitored by TLC), reaction solvent was removed under reduced pressure. The crude compound was purified by column chromatography on silica gel (100/200 mesh) using petroleum ether (60-80) and ethyl acetate as eluent which yielded the product as yellow color oil (5.1 g, Yield: 83.3%): MS (ESI, 120 eV): m/z=375.1 (M+H)+; 1H NMR (300 MHz, CDCl3): δ 7.68 (s, 1H), 7.62-7.66 (d, 3H), 7.57-7.59 (d, 1H), 7.53 (m, 1H), 7.45-7.50 (m, 3H), 7.11-7.13 (d, 2H), 6.88-6.90 (d, 2H), 5.10 (s, 2H), 3.66 (s, 3H), 2.85-2.92 (m, 2H), 2.56-2.62 (m, 2H).

Aufarbeitung

  1. customTo a 250 mL RB flask fitted with magnetic stirrer
  2. stirringstirring
  3. waitcontinued at RT for 24 h
  4. customAfter completion of the reaction (reaction monitored by TLC), reaction solvent
  5. customwas removed under reduced pressure
  6. customThe crude compound was purified by column chromatography on silica gel (100/200 mesh)

Quellen und Nachweise

ORD-Eintrag
ord-ef92470ef89f417582c29d0fbf27735f
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09278915B2

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