4-Hydroxybenzoic Acid → 4-Hydroxy-3-iodobenzoic acid (2IPCOOH)

HRID 1602694Notes

Reaction equation

HRID 1602694 reaction equation
Cl([O-])(=O)(=O)=O.[Na+].[OH:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=1.[OH-].[Na+].[I-:19].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+].Cl>CO>[I:19][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:8]=1[OH:7])[C:12]([OH:14])=[O:13]

Participants

8

Reactant 6

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

Product 1

HCID 4494734-Hydroxy-3-iodobenzoic acid (2IPCOOH)

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 (12.75 g, 0.92 mol), sodium hydroxide (3.7 g, 0.92 mol) and sodium iodide (13.85 g, 0.92 mol) in methanol (350 ml) at 0° C. The mixture is left stirring for two hours at 0° C. 100 ml of 10% sodium thiosulphate solution are added. After stirring, the mixture is acidified with hydrochloric acid to pH 1. It is extracted with 600 ml of ethyl ether. The organic phase is washed twice with 400 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 600 ml of ethyl ether
  4. washThe organic phase is washed twice with 400 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-dbc4573fd7354556bf22ecacf76230e5
Source dataset
uspto-grants-1999_11
Patent number
US05981776

Reaction notes

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