Water → 2-Cyclopentylbenzoic acid

HRID 334047Notes

Reaction equation

HRID 334047 reaction equation
[OH-].[Li+].O.C([O:6][C:7](=[O:19])[C:8]1[C:13]([CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:12][CH:11]=[CH:10][CH:9]=1)C.[OH-].[Na+]>C1COCC1>[CH:14]1([C:13]2[C:8]([C:7]([OH:19])=[O:6])=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:15][CH2:16][CH2:17][CH2:18]1

Participants

6

Reactant 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 14798Sodium HydroxideHCID 866882776-Cyclopentyl-benzoic acid ethyl ester

Product 1

HCID 227631552-Cyclopentylbenzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.200 g (8.35 mmol) lithium hydroxide and 15 mL water were added to a solution of 1.10 g (5.04 mmol) 6-cyclopentyl-benzoic acid ethyl ester in 20 mL THF at RT, and the resulting mixture was stirred over night. 5.00 mL (20.0 mmol) 4 M aqueous NaOH solution were added and stirring was continued at 50° C. for 5 h. THF was removed by distillation. The residue was acidified with 4 M aqueous hydrochlorid and the precipitate was filtered off, washed with water and dried.

Workup

  1. stirringstirring
  2. customTHF was removed by distillation
  3. filtrationthe precipitate was filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-c98b00b90a4a4896a4b6ecdb9feaf248
Source dataset
uspto-grants-2014_11
Patent number
US08883789B2

Reaction notes

Loading…