Water → Isobutyl 2-hydroxy-5-iodobenzoate

HRID 1653895Notes

Reaction equation

HRID 1653895 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH2:12](O)[CH:13]([CH3:15])[CH3:14].S(=O)(=O)(O)O.O>C1(C)C=CC=CC=1>[OH:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4]([O:6][CH2:12][CH:13]([CH3:15])[CH3:14])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 6560IsobutanolHCID 83885-Iodosalicylic acid

Product 1

HCID 19423370Isobutyl 2-hydroxy-5-iodobenzoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-hydroxy-5-iodobenzoic acid (477 g, 1.8 mol), isobutanol (225 g), conc sulfuric acid (20 ml) in toluene (2 l) was refluxed for 6 h using a water separator. The solution was cooled and washed with water. The solution was treated with decolorizing carbon and the toluene was evaporated. The residue was recrystallized from methanol. Yield 376 g.

Workup

  1. temperatureThe solution was cooled
  2. washwashed with water
  3. additionThe solution was treated with decolorizing carbon
  4. customthe toluene was evaporated
  5. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-aba77bbe47544df3878f92ebd14df2b7
Source dataset
uspto-grants-1995_04
Patent number
US05403930

Reaction notes

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