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

HRID 30858

反応式

HRID 30858 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
40 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-9cd8ad47dedb461dbc8db9536abd9c15
出典データセット
uspto-grants-2008_09
特許番号
US07423156B2

関連ノート

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