Sodium Hydroxide → 5-Cyano-2-iodobenzoic acid

HRID 321998Notes

Reaction equation

HRID 321998 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:15])[C:6]1[CH:11]=[C:10]([C:12]#[N:13])[CH:9]=[CH:8][C:7]=1[I:14]>O.CO>[I:14][C:7]1[CH:8]=[CH:9][C:10]([C:12]#[N:13])=[CH:11][C:6]=1[C:5]([OH:15])=[O:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 23076822Methyl 5-cyano-2-iodobenzoate

Product 1

HCID 220088225-Cyano-2-iodobenzoic acidYield 66.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of sodium hydroxide (0.44 g, 11 mmol) in water (10 ml) was added to 2-iodo-5-cyanobenzoic acid methyl ester (2.7 g, 9.4 mmol) in methanol. The mixture was stirred for 20 h, then most of the solvent was evaporated and the residue acidified with 2N hydrochloric acid. The resulting precipitate was filtered off and dried to give a white solid (1.7 g). MS (−CI) m/z 272 [M-H]+.

Workup

  1. custommost of the solvent was evaporated
  2. filtrationThe resulting precipitate was filtered off
  3. customdried

Sources & evidence

ORD record
ord-d0e0c6c8931248808b8d7128df7ffa4f
Source dataset
uspto-grants-2001_04
Patent number
US06211189B1

Reaction notes

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