Toluene → 2-{4-(4-Methoxyphenyl) phenyl}ethylbenzylether

HRID 1457493

Reaktionsgleichung

Reaktionsgleichung von HRID 1457493
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:13](O)=O)[C:10](O)=O)=[CH:5][CH:4]=1.BrC1C=[CH:21][C:20]([CH2:23][CH2:24][O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:19]C=1.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:10]=[CH:19][C:20]([CH2:23][CH2:24][O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:21][CH:13]=2)=[CH:7][CH:8]=1

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 13716680(4-Methoxyphenyl)propanedioic acidHCID 219093031-(2-(Benzyloxy)ethyl)-4-bromobenzene

Produkt 1

HCID 539553012-{4-(4-Methoxyphenyl) phenyl}ethylbenzyletherAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

1.57 g (10.3 mmol) of 4-methoxyphenyl malonic acid, 3.0 g (10.3 mmol) of 2-(4-bromophenyl) ethylbenzylether, 0.38 g of tetrakis (triphenylphosphine) palladium, 15 ml of 2M-sodium carbonate solution, 15 ml of toluene and 10 ml of ethanol were heated at 80° C. for 4 hours under presence of nitrogen. After reactions had been completed, extraction with toluene was performed. Then, the extracted solution was dried with anhydrous sodium sulfate. The solvent was removed by filtration, and then refining was performed with a silica gel column chromatography (developing solvent: toluene) and by recrystallization (ethanol) so that 2.63 g of 2-{4-(4-methoxyphenyl) phenyl}ethylbenzylether was obtained (yield 80%).

Aufarbeitung

  1. extractionextraction with toluene
  2. dry with materialThen, the extracted solution was dried with anhydrous sodium sulfate
  3. customThe solvent was removed by filtration
  4. customrefining was performed with a silica gel column chromatography (developing solvent: toluene) and by recrystallization (ethanol) so that 2.63 g of 2-{4-(4-methoxyphenyl) phenyl}ethylbenzylether
  5. customwas obtained (yield 80%)

Quellen und Nachweise

ORD-Eintrag
ord-1e0e22335e2e4f16abe1f43970468c0b
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05849217

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