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

HRID 9550Notes

Reaction equation

HRID 9550 reaction equation
[OH-].[Na+].C[O:4][C:5]([C@@H:7]1[CH2:11][CH2:10][CH2:9][C@@H:8]1[C:12](=[O:20])[C:13]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][CH:14]=1)=[O:6]>O.CO>[Br:19][C:16]1[CH:15]=[CH:14][C:13]([C:12]([C@@H:8]2[CH2:9][CH2:10][CH2:11][C@H:7]2[C:5]([OH:6])=[O:4])=[O:20])=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67147310cis-2-(4-Bromobenzoyl)cyclopentanecarboxylic acid methyl ester

Product 1

HCID 23549251trans-2-(4-Bromobenzoyl)cyclopentanecarboxylic acidYield 83%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of NaOH (128.2 g, 3.2 mol) in 700 mL water was added to a solution of cis-2-(4-bromo-benzoyl)-cyclopentanecarboxylic acid methyl ester (166.3 g, 534.3 mmol) in MeOH (700 mL). The reaction mixture was stirred at rt overnight. NMR analysis showed that little starting material remained. After ca. 1 L solvent was removed by rotary evaporation, the mixture was diluted with 1 L water. Conc. HCl was slowly added with stirring at <15° C., to adjust the acidity to pH <6. A precipitate formed, and stirring was continued for 1 h. The solid precipitate was filtered, and rinsed with water. The dried filter cake was dissolved in 1 L EtOAc, and dried over Na2SO4. Removal of solvent and drying in vacuo afforded the desired product (131 g, 83%). 1H NMR (CDCl3) δ 7.83 (d, 2H), 7.60 (d, 2H), 4.05 (m, 1H), 3.50 (m, 1H), 2.20 (m, 2H), 2.00 (m, 1H), 1.78 (m, 3H).

Workup

  1. customAfter ca. 1 L solvent was removed by rotary evaporation
  2. additionthe mixture was diluted with 1 L water
  3. additionConc. HCl was slowly added
  4. stirringwith stirring at <15° C.
  5. customA precipitate formed
  6. stirringstirring
  7. waitwas continued for 1 h
  8. filtrationThe solid precipitate was filtered
  9. washrinsed with water
  10. filtrationThe dried filter cake
  11. dissolutionwas dissolved in 1 L EtOAc
  12. dry with materialdried over Na2SO4
  13. customRemoval of solvent
  14. customdrying in vacuo

Sources & evidence

ORD record
ord-c22397a0792547ccbaedca4a5b962ebd
Source dataset
uspto-grants-2006_08
Patent number
US07091228B2

Reaction notes

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