Sodium Hydroxide → 5-Cyano-2-iodobenzoic acid

HRID 2287346Notes

Reaction equation

HRID 2287346 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-2264b98e007e4a1daf8e6345d8bb6f21
Source dataset
uspto-grants-2000_07
Patent number
US06083952

Reaction notes

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