Sodium Iodide → 3-tert-Butyl-4-hydroxy-5-iodobenzoic Acid

HRID 2377195Notes

Reaction equation

HRID 2377195 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[OH:14])[C:8]([OH:10])=[O:9])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[I-:17].[Na+].Cl[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>CO>[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([I:17])[C:13]=1[OH:14])[C:8]([OH:10])=[O:9])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 14798Sodium HydroxideHCID 24477Sodium ThiosulfateHCID 144015103-tert-Butyl-4-hydroxybenzoic acidHCID 23665760Sodium Hypochlorite

Product 1

HCID 120848143-tert-Butyl-4-hydroxy-5-iodobenzoic AcidYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

20 g (103 mmol) of 3-tert-butyl-4-hydroxybenzoic acid are dissolved in 400 mL of methanol. 4.12 g (103 mmol) of sodium hydroxide and 15.4 g (103 mmol) of sodium iodide are added. The reaction medium is cooled to 0° C., and 234 g (113 mmol) of 3.6% sodium hypochlorite are added slowly. The medium is stirred at 0° C. for 2 hours and is then treated with saturated sodium thiosulfate solution. The aqueous phase is acidified and extracted with ethyl ether. A pale yellow solid is obtained (m=24.7 g; yield=75%; m.p.=178° C.).

Workup

  1. extractionextracted with ethyl ether
  2. customA pale yellow solid is obtained (m=24.7 g; yield=75%; m.p.=178° C.)

Sources & evidence

ORD record
ord-9bfa1c026c45420189593361983a8901
Source dataset
uspto-grants-2008_12
Patent number
US07468457B2

Reaction notes

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