Dimethylformamide → Methyl 4'-methoxy(1,1'-biphenyl)-4-carboxylate

HRID 493503

Reaktionsgleichung

Reaktionsgleichung von HRID 493503
[CH2:1](N(CC)CC)C.O[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([OH:23])=[O:22])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+].IC.CN([CH:35]=[O:36])C>C(Cl)Cl>[CH3:1][O:23][C:21]([C:18]1[CH:19]=[CH:20][C:15]([C:12]2[CH:13]=[CH:14][C:9]([O:36][CH3:35])=[CH:10][CH:11]=2)=[CH:16][CH:17]=1)=[O:22]

Komponenten

7

Edukt 5

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 3015564'-Hydroxy-4-biphenylcarboxylic acid

Produkt 1

HCID 1393415Methyl 4'-methoxy(1,1'-biphenyl)-4-carboxylateAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Triethylamine (9.76 mL, 70 mmol) was added under nitrogen to a solution of 4′-hydroxy-biphenyl-4-carboxylic acid (15.0 g, 70 mmol) in 200 mL of anhydrous DMF at room temperature. After stirring for 5 minutes potassium carbonate (58.0 g, 420 mmol) was added and the reaction stirred an additional 5 minutes. Iodomethane (26.0 mL, 420 mmol) was then added (exothermic reaction) and the reaction stirred overnight. The reaction was diluted with methylene chloride, extracted multiple times with water, dried (MgSO4) and the solvent removed under reduced pressure to give 4′-methoxy-biphenyl-4-carboxylic acid methyl ester (16.26 g, 96%) as a tan solid, mp 170-173° C. Elemental Analysis for C15H14O3: Calc'd: C, 74.36; H, 5.82; N, 0.00; Found: C, 73.97; H, 5.66; N, 0.03.

Aufarbeitung

  1. additionwas added
  2. custom(exothermic reaction)
  3. stirringthe reaction stirred overnight
  4. extractionextracted multiple times with water
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7593faf78e8b464daa4635e444d5e85d
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07534894B2

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