Sodium Hydroxide → trans-2-(4-Bromobenzoyl)cyclopropanecarboxylic acid

HRID 9543

Reaktionsgleichung

Reaktionsgleichung von HRID 9543
[Br:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C@H:8]2[CH2:10][C@H:9]2[C:11]([O:13]C)=[O:12])=[O:7])=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C@@H:8]2[CH2:10][C@H:9]2[C:11]([OH:13])=[O:12])=[O:7])=[CH:15][CH:16]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 67147290Methyl cis-2-(4-bromobenzoyl)cyclopropanecarboxylate

Produkt 1

HCID 58681322trans-2-(4-Bromobenzoyl)cyclopropanecarboxylic acidAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

Methyl cis-2-(4-bromobenzoyl)cyclopropanecarboxylate (10.34 g, 36.52 mmol) was dissolved in MeOH (100 mL), and then 15 mL 50% aqueous NaOH solution was added. The reaction mixture was stirred at 40° C. for 3 days. Solvent was removed by rotary evaporation and the residue was dissolved in water. Concentrated HCl was added to adjust the acidity to pH 1. The precipitate that formed was collected by filtration and dried in a vacuum oven overnight to give trans-2-(4-bromobenzoyl)cyclopropanecarboxylic acid (9.43 g, 95%). LC-MS ret. time 2.51, m/z 270 (MH+); 1H NMR (400 MHz, CD2Cl2) δ 1.68 (m, 2H), 2.38 (m, 1H), 3.22 (m, 1H), 7.67 (m, 2H), 7.90 (m, 2H).

Aufarbeitung

  1. customSolvent was removed by rotary evaporation
  2. dissolutionthe residue was dissolved in water
  3. additionConcentrated HCl was added
  4. customThe precipitate that formed
  5. filtrationwas collected by filtration
  6. customdried in a vacuum oven overnight

Quellen und Nachweise

ORD-Eintrag
ord-62d31b89ec784a0aa8451b3f2a6e1fb5
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091228B2

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