Sodium Hydroxide → HCID 69361512, compound

HRID 2181677Notes

Reaction equation

HRID 2181677 reaction equation
[CH:1]([C:4]1[C:8]2[CH:9]=[C:10]([C:13]([O:15]C)=[O:14])[CH:11]=[CH:12][C:7]=2[O:6][CH:5]=1)([CH3:3])[CH3:2].[OH-].[Na+]>CO.O>[CH:1]([C:4]1[C:8]2[CH:9]=[C:10]([C:13]([OH:15])=[O:14])[CH:11]=[CH:12][C:7]=2[O:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22481728HCID 22481728, compound

Product 1

HCID 69361512HCID 69361512, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl 3-isopropyl-1-benzofuran-5-carboxylate (1.20 g, 5.51 mmol) is dissolved in MeOH (20 ml) and water (4 ml), treated drop-wise with 2N NaOH (3.3 ml, 6.6 mmol) and stirred at RT for 2 days, then at 40° C. for 4 h. The volatiles are removed in vacuo, the residue is dissolved in water (10 ml) and the pH is adjusted to 3 with concentrated HCl. The resulting precipitate is isolated via filtration and dried overnight to afford 1.08 g (97%) of 3-isopropyl-1-benzofuran-5-carboxylic acid as a white solid. MS (ESI−) for C12H12O3 m/z: 203.0 (M−H)−.

Workup

  1. waitat 40° C. for 4 h
  2. customThe volatiles are removed in vacuo
  3. dissolutionthe residue is dissolved in water (10 ml)
  4. customThe resulting precipitate is isolated via filtration
  5. customdried overnight

Sources & evidence

ORD record
ord-872d0176cf8b4d5a9b4aa67f1eec1f3a
Source dataset
uspto-grants-2005_05
Patent number
US06894042B2

Reaction notes

Loading…