Hydrochloric Acid → 4'-Methoxy(1,1'-biphenyl)-4-carboxylic acid

HRID 493504

Reaktionsgleichung

Reaktionsgleichung von HRID 493504
[OH-].[Na+].C[O:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)=[O:6].O.Cl>C1COCC1>[CH3:20][O:19][C:16]1[CH:15]=[CH:14][C:13]([C:10]2[CH:11]=[CH:12][C:7]([C:5]([OH:6])=[O:4])=[CH:8][CH:9]=2)=[CH:18][CH:17]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 1393415Methyl 4'-methoxy(1,1'-biphenyl)-4-carboxylate

Produkt 1

HCID 27595524'-Methoxy(1,1'-biphenyl)-4-carboxylic acidAusbeute 98,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

1 N NaOH (148.5 mL, 148.5 mmol) was added under nitrogen to a solution of 4′-methoxy-biphenyl-4-carboxylic acid methyl ester (12.0 g, 49.5 mmol), prepared in the previous step, in 1 L of THF plus 250 mL of water at room temperature. After the addition the reaction was refluxed for 16.5 h (overnight). After cooling to approximately room temperature the reaction was acidified by the addition of 1 N HCl and then concentrated under reduced pressure. The solid that formed was collected by filtration and dried under reduced pressure to give 4′-methoxy-biphenyl-4-carboxylic acid (11.11 g, 98%) as a white solid, mp 245-250° C.; MS (ESI) m/z 227 [M−H]−. Elemental Analysis for C14H12O3: Calc'd: C, 73.67; H, 5.30; N, 0.00; Found: C, 69.52; H, 5.01; N, 0.04.

Aufarbeitung

  1. customat room temperature
  2. additionAfter the addition the reaction
  3. temperaturewas refluxed for 16.5 h (overnight)
  4. temperatureAfter cooling to approximately room temperature the reaction
  5. concentrationconcentrated under reduced pressure
  6. customThe solid that formed
  7. filtrationwas collected by filtration
  8. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-18d9b68ed9d446ad8c916716710e890f
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07534894B2

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