Sodium Hydroxide → 3-Cyclopropyl-5-methoxybenzoic acid

HRID 502451Notes

Reaction equation

HRID 502451 reaction equation
C[O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[C:6]([CH:12]2[CH2:14][CH2:13]2)[CH:5]=1.[OH-].[Na+]>C1COCC1.C(O)C>[CH:12]1([C:6]2[CH:5]=[C:4]([CH:9]=[C:8]([O:10][CH3:11])[CH:7]=2)[C:3]([OH:15])=[O:2])[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68459588HCID 68459588, compound

Product 1

HCID 684548573-Cyclopropyl-5-methoxybenzoic acidYield 98.2%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

The above prepared 3-cyclopropyl-5-methoxy-benzoic acid methyl ester (0.221 g, 1.07 mmol) was dissolved in 3.6 ml of THF/ethanol=1/1 and treated with 1.79 ml of aq. NaOH (3M, 5 eq.). The mixture was stirred for 1.5 h at ambient temperature and was then poured onto crashed ice/AcOEt/HCl dil.; the organic layer was washed with water, dried over sodium sulfate, and evaporated to dryness to leave 0.202 g of the title compound as white solid.

Workup

  1. additionwas then poured
  2. washthe organic layer was washed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-edf3cd432fb348e48c8a147ae9c641a4
Source dataset
uspto-grants-2010_08
Patent number
US07772253B2

Reaction notes

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