Water → Isobutyl 2-hydroxy-5-iodobenzoate

HRID 742998Notes

Reaction equation

HRID 742998 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), cone sulfuric acid (20 ml) in toluene (21) 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-0bb0f3b7f396445a884c57d8cf7b8be0
Source dataset
uspto-grants-1996_09
Patent number
US05556855

Reaction notes

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