Sodium Hydroxide → HCID 69795068, compound

HRID 2181668Notes

Reaction equation

HRID 2181668 reaction equation
[CH2:1]([O:3][CH:4]([O:18][CH2:19][CH3:20])[C:5]1[O:6][C:7]2[CH:13]=[C:12]([C:14]([O:16]C)=[O:15])[CH:11]=[CH:10][C:8]=2[CH:9]=1)[CH3:2].[OH-].[Na+]>CO.O>[CH2:19]([O:18][CH:4]([O:3][CH2:1][CH3:2])[C:5]1[O:6][C:7]2[CH:13]=[C:12]([C:14]([OH:16])=[O:15])[CH:11]=[CH:10][C:8]=2[CH:9]=1)[CH3:20]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22481729HCID 22481729, compound

Product 1

HCID 69795068HCID 69795068, compoundYield 103.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl 2-(diethoxymethyl)-1-benzofuran-6-carboxylate (417 mg, 1.5 mmol) is dissolved in MeOH (8 ml) and H2O (2 ml). 2N NaOH (0.9 ml, 1.8 mmol) is added drop-wise, and the reaction is stirred for 4 days. The volatiles are removed in vacuo and the residue is dissolved in H2O (2 ml). Concentrated HCl is used to adjust the pH to 3, and the resulting precipitate is isolated via filtration and dried overnight to afford 410 mg (>100%, water present) of 2-(diethoxymethyl)-1-benzofuran-6-carboxylic acid as a brown solid. 1H NMR (400 MHz, CDCl3): δ 1.29, 3.72, 6.9, 7.66, 8.04, 8.29 ppm.

Workup

  1. customThe volatiles are removed in vacuo
  2. dissolutionthe residue is dissolved in H2O (2 ml)
  3. customthe resulting precipitate is isolated via filtration
  4. customdried overnight

Sources & evidence

ORD record
ord-dc04a162a7ca4bdaac9b5d1b589b17c0
Source dataset
uspto-grants-2005_05
Patent number
US06894042B2

Reaction notes

Loading…