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

HRID 9543

반응식

HRID 9543 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
40 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-62d31b89ec784a0aa8451b3f2a6e1fb5
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091228B2

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