Sodium Hydroxide → 2-(Benzyloxy)-4-iodobenzoic acid

HRID 454458Notes

Reaction equation

HRID 454458 reaction equation
[OH-].[Na+].[CH2:3]([O:10][C:11]1[CH:20]=[C:19]([I:21])[CH:18]=[CH:17][C:12]=1[C:13]([O:15]C)=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>O1CCOCC1.CO>[CH2:3]([O:10][C:11]1[CH:20]=[C:19]([I:21])[CH:18]=[CH:17][C:12]=1[C:13]([OH:15])=[O:14])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66990993Methyl 2-(benzyloxy)-4-iodobenzoate

Product 1

HCID 571301542-(Benzyloxy)-4-iodobenzoic acidYield 96.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A 2.0 mol/L aqueous solution of sodium hydroxide (4.1 mL) was added to a solution mixture of methyl 2-(benzyloxy)-4-iodobenzoate (1.0 g) in dioxane (5.0 mL) and methanol (5.0 mL), followed by stirring at room temperature for 2 hours. The solvent was evaporated under reduced pressure, and water was added to the residue. After adjusting the pH to 2.5 with 6.0 mol/L hydrochloric acid under ice-cooling, ethyl acetate was added. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. Hexane and diisopropyl ether were added to the obtained residue, and the resulting solid substance was collected by filtration to obtain 0.93 g of 2-(benzyloxy)-4-iodobenzoic acid as a white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure, and water
  2. additionwas added to the residue
  3. temperaturecooling
  4. additionethyl acetate was added
  5. customThe organic layer was separated
  6. washwashed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. additionHexane and diisopropyl ether were added to the obtained residue
  10. filtrationthe resulting solid substance was collected by filtration

Sources & evidence

ORD record
ord-f70b56d5ba6440a390bdc5caca70f5ff
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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