Sodium Hydroxide → HCID 69794916, compound

HRID 2181680Notes

Reaction equation

HRID 2181680 reaction equation
[Cl:1][C:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([O:13]CC)=[O:12])=[CH:10][C:5]=2[O:4][CH:3]=1.[OH-].[Na+]>CO.O>[Cl:1][C:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([OH:13])=[O:12])=[CH:10][C:5]=2[O:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22481771Ethyl 3-chloro-6-benzofurancarboxylate

Product 1

HCID 69794916HCID 69794916, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Ethyl 3-chloro-1-benzofuran-6-carboxylate (110 mg, 0.49 mmol) is dissolved in MeOH (3 ml) and water (0.75 ml), treated drop-wise with 2N NaOH (0.27 ml, 0.54 mmol) and stirred overnight at RT. The volatiles are removed in vacuo, the residue is dissolved in water (3 ml) and the pH is adjusted to 3 with concentrated HCl. The resulting solid is filtered and dried overnight in a vacuum oven to afford 88 mg (92%) of 3-chloro-1-benzofuran-6-carboxylic acid as a white solid. MS for C9H5ClO3 (EI) m/z: 196(M)+.

Workup

  1. customThe volatiles are removed in vacuo
  2. dissolutionthe residue is dissolved in water (3 ml)
  3. filtrationThe resulting solid is filtered
  4. customdried overnight in a vacuum oven

Sources & evidence

ORD record
ord-9e88f6d342a74d40a9764c4c63217e6d
Source dataset
uspto-grants-2005_05
Patent number
US06894042B2

Reaction notes

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