Sodium Hydroxide → (5-Cyclopropyl-2,4-dimethyl-phenyl)-acetic acid

HRID 1962368Notes

Reaction equation

HRID 1962368 reaction equation
C[O:2][C:3](=[O:16])[CH2:4][C:5]1[CH:10]=[C:9]([CH:11]2[CH2:13][CH2:12]2)[C:8]([CH3:14])=[CH:7][C:6]=1[CH3:15].[OH-].[Na+]>CO>[CH:11]1([C:9]2[C:8]([CH3:14])=[CH:7][C:6]([CH3:15])=[C:5]([CH2:4][C:3]([OH:16])=[O:2])[CH:10]=2)[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59614579(5-Cyclopropyl-2,4-dimethyl-phenyl)-acetic acid methyl ester

Product 1

HCID 59614593(5-Cyclopropyl-2,4-dimethyl-phenyl)-acetic acidYield 98.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.5 g of (5-cyclopropyl-2,4-dimethyl-phenyl)-acetic acid methyl ester in 30 ml of methanol was kept at ice bath temperature and treated with 0.5 g of sodium hydroxide in 5 portions. The reaction mixture was stirred at room temperature for 1.5 hours. The solvent was removed in vacuo, the residue poured into water and extracted with diethyl ether. The combined organic phases were dried with sodium sulfate, filtered and concentrated to afford 2.3 g of (5-cyclopropyl-2,4-dimethyl-phenyl)-acetic acid.

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue poured into water
  3. extractionextracted with diethyl ether
  4. dry with materialThe combined organic phases were dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ccc0ac7a637f4331bd30443462201ccb
Source dataset
uspto-grants-2013_04
Patent number
US08415369B2

Reaction notes

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