Sulfuric Acid → Propan-2-yl 2-hydroxy-5-iodobenzoate

HRID 1464160Notes

Reaction equation

HRID 1464160 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].S(=O)(=O)(O)O.[C:17]1(C)[CH:22]=CC(S(O)(=O)=O)=C[CH:18]=1>C1(C)C=CC=CC=1.CC(O)C.O>[OH:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4]([O:6][CH:17]([CH3:22])[CH3:18])=[O:5]

Participants

7

Reactant 3

HCID 1118Sulfuric AcidHCID 6101p-Toluenesulfonic acidHCID 83885-Iodosalicylic acid

Product 1

HCID 19423422Propan-2-yl 2-hydroxy-5-iodobenzoate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 3776IsopropanolSolvent3×

Procedure

2-Hydroxy-5-iodobenzoic acid (I 84 g, 0.7 mol), isopropanol (50 ml), conc sulfuric acid (5 ml) and p-toluenesulfonic acid (10 g) in toluene (1 1) was refluxed using a water separator. Portions of isopropanol was added intermittently to compensate for loss of 2-propanol by dehydration. After 24 h, the solution was cooled and washed with water. The toluene was evaporated partially. Iso-octane was added, and precipitated 2-hydroxy-5-iodobenzoic acid (106 g) filtered off. The solution was taken to dryness and the residue recrystallized from methanol. Yield 64 g, (71%), corrected for recovered starting material).

Workup

  1. temperaturethe solution was cooled
  2. washwashed with water
  3. customThe toluene was evaporated partially
  4. additionIso-octane was added
  5. customprecipitated 2-hydroxy-5-iodobenzoic acid (106 g)
  6. filtrationfiltered off
  7. customthe residue recrystallized from methanol
  8. customfor recovered starting material)

Sources & evidence

ORD record
ord-cd2a8d553ab046aca3e9ccade053fe01
Source dataset
uspto-grants-1994_04
Patent number
US05302718

Reaction notes

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