Potassium Hydroxide → HCID 17957013, compound

HRID 2186411Notes

Reaction equation

HRID 2186411 reaction equation
[OH-].[K+].[I:3][C:4]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][Si](C)(C)C)=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]>CO>[I:3][C:4]1[CH:12]=[CH:11][C:10]([C:13]#[CH:14])=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 11089200HCID 11089200, compound

Product 1

HCID 17957013HCID 17957013, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4.5 ml of aqueous potassium hydroxide solution (1 N) are added at 0° C. to a solution of 500 mg of 2-iodo-5-trimethylsilylethynylbenzoic acid (1.45 mmol, 1 eq.) in 30 ml of methanol. After stirring for 2 h at room temperature, the reaction medium is washed with 2×50 ml of CH2Cl2 and the aqueous phase is then reacidified to pH 2 by the addition of molar hydrochloric acid solution. After extraction with 2×50 ml of CH2Cl2, the organic phases are combined, dried and evaporated to give 383 mg of 2-iodo-5-ethynylbenzoic acid in the form of a yellow solid (yield: 97%).

Workup

  1. washthe reaction medium is washed with 2×50 ml of CH2Cl2
  2. additionthe aqueous phase is then reacidified to pH 2 by the addition of molar hydrochloric acid solution
  3. extractionAfter extraction with 2×50 ml of CH2Cl2
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-f2e6e710bedc4edc821f343003fde17a
Source dataset
uspto-grants-2002_06
Patent number
US06403705B1

Reaction notes

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