Sodium Chloride → 2-Hydroxy-5-iodo-3-methylbenzoic acid

HRID 1916564Notes

Reaction equation

HRID 1916564 reaction equation
Cl[O-].[Na+].[OH:4][C:5]1[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:6]=1[C:7]([O:9]C)=[O:8].[Na+].[I-:17].[OH-].[Na+].[Na+].[Cl-]>CO.O.C(Cl)Cl>[OH:4][C:5]1[C:14]([CH3:15])=[CH:13][C:12]([I:17])=[CH:11][C:6]=1[C:7]([OH:9])=[O:8]

Participants

9

Reactant 5

HCID 5234Sodium ChlorideHCID 5238Sodium IodideHCID 14798Sodium HydroxideHCID 31835Benzoic acid, 2-hydroxy-3-methyl-, methyl esterHCID 23665760Sodium Hypochlorite

Product 1

HCID 159086852-Hydroxy-5-iodo-3-methylbenzoic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-5 °C

Procedure

14.9 mL (24.1 mmol) sodium hypochlorite solution (10 percent by weight in water) is added dropwise to a solution of 4.0 g (24.1 mmol) methyl 2-hydroxy-3-methyl-benzoate, 3.6 g (24.1 mmol) NaI, 0.96 g (24.1 mmol) NaOH in 100 mL MeOH at −5° C. over 40 min. The reaction is stirred for 30 min at −5° C. and 5 days at RT. The solvent is eliminated i.vac. and the residue is taken up in 80 mL water and 50 mL DCM. After the organic phase has been saturated with NaCl it is extracted twice with DCM. The combined organic extracts are filtered and the solvent is eliminated i.vac. The product is further reacted without any more purification.

Workup

  1. extractionis extracted twice with DCM
  2. filtrationThe combined organic extracts are filtered
  3. customThe product is further reacted without any more purification

Sources & evidence

ORD record
ord-638b86c89d4a4a29b79d882457ac8a43
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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