Sulfuric Acid → 4-Iodo-3-methylbenzoic acid

HRID 1136

Reaction equation

HRID 1136 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1N)[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.N([O-])=O.[Na+].[I-:21].[K+]>O.C(OCC)(=O)C.[Cu](I)I>[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[I:21])[C:5]([OH:7])=[O:6]

Participants

8

Reactant 4

HCID 1118Sulfuric Acid2×HCID 4875Potassium IodideHCID 755984-Amino-3-methylbenzoic acidHCID 23668193Sodium Nitrite

Product 1

HCID 15173224-Iodo-3-methylbenzoic acid

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

20 g (0.132 mol) of 3-methyl-4-aminobenzoic acid and 175 ml of sulfuric acid (20%) were introduced into a three-necked flask. At -10° C., a solution of 11.9 g (0.172 mol) of sodium nitrite in 50 ml of water was added dropwise and the mixture was stirred for two hours. This solution was introduced dropwise via a dropping funnel cooled to -5° C. into a solution of 35 g (0.211 mol) of potassium iodide, 35.2 g (0.185 mol) of copper iodide and 175 ml of sulfuric acid (20%). The mixture was stirred for eight hours, and the reaction medium filtered. The solids obtained were dissolved in ethyl acetate, washed with water and then with a sodium sulfite solution, dried over magnesium sulfate and evaporated. 24.4 g (70%) of 3-methyl-4-iodobenzoic acid of melting point 205°-210° C. were recovered.

Workup

  1. additionThis solution was introduced dropwise via a dropping funnel
  2. stirringThe mixture was stirred for eight hours
  3. customThe solids obtained
  4. washwashed with water
  5. dry with materialwith a sodium sulfite solution, dried over magnesium sulfate
  6. customevaporated
  7. custom24.4 g (70%) of 3-methyl-4-iodobenzoic acid of melting point 205°-210° C. were recovered

Sources & evidence

ORD record
ord-af764768aabb4d659aa7d8d3f6f94944
Source dataset
uspto-grants-1998_03
Patent number
US05723499

Linked notes

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