4-Hydroxybenzoic Acid → 3-Hydroxy-4-iodobenzoic acid

HRID 1602688Notes

Reaction equation

HRID 1602688 reaction equation
Cl([O-])(=O)(=O)=O.[Na+].O[C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=1.[OH-:17].[Na+].[I-:19].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+].Cl>CO>[I:19][C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]=1[OH:17]

Participants

8

Reactant 6

HCID 1354-Hydroxybenzoic AcidHCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 14798Sodium HydroxideHCID 24477Sodium ThiosulfateHCID 522606Sodium Perchlorate

Product 1

HCID 7368543-Hydroxy-4-iodobenzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

3.6% sodium perchlorate solution is added dropwise to a mixture of 4-hydroxybenzoic acid (2.55 g, 18.5 mmol), sodium hydroxide (0.74 g, 18.5 mmol) and sodium iodide (2.77 g, 18.5 mmol) in methanol (50 ml), at 0° C. The mixture is left stirring for two hours at 0° C. 20 ml of 10% sodium thiosulphate solution are added. After stirring, the mixture is acidified with hydrochloric acid to pH 1. It is extracted with 100 ml of ethyl ether. The organic phase is washed twice with 80 ml of water, dried over magnesium sulphate and concentrated on a rotary evaporator under vacuum at 40° C.

Workup

  1. waitThe mixture is left
  2. stirringAfter stirring
  3. extractionIt is extracted with 100 ml of ethyl ether
  4. washThe organic phase is washed twice with 80 ml of water
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated on a rotary evaporator under vacuum at 40° C.

Sources & evidence

ORD record
ord-ce10187c307048bf81859c4eb15964f2
Source dataset
uspto-grants-1999_11
Patent number
US05981776

Reaction notes

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