2-Iodo-5-methylbenzoic acid → Benzoic acid, 2-iodo-5-methyl-, methyl ester

HRID 432673Notes

Reaction equation

HRID 432673 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:12]C(C)(C)C([O-])([O-])[O-]>C1(C)C=CC=CC=1.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>[I:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1[C:4]([O:6][CH3:12])=[O:5]

Participants

6

Reactant 2

HCID 1429412-Iodo-5-methylbenzoic acidHCID 21927715Trimethylorthoacetate

Product 1

HCID 14263946Benzoic acid, 2-iodo-5-methyl-, methyl ester

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 2-iodo-5-methyl benzoic acid (10.0 g, 0.038 mol) in toluene (200 mL) was added trimethylorthoacetate (25 mL) at room temperature. The reaction mixture was refluxed for 12 hours. The reaction mixture was cooled to room temperature and diluted with saturated sodium bicarbonate and ethyl acetate. The layers were separated and the organic layer washed with brine. The organic layer was dried (MgSO4) and solvent removed to give 10.35 g of methyl 2-iodo-5-methylbenzoate (EX-25A) as a yellow oil with an m/z+1=277.

Workup

  1. temperatureThe reaction mixture was refluxed for 12 hours
  2. customThe layers were separated
  3. washthe organic layer washed with brine
  4. dry with materialThe organic layer was dried (MgSO4) and solvent
  5. customremoved

Sources & evidence

ORD record
ord-ce0c0153be1f4a818b5217e3a5e91629
Source dataset
uspto-grants-2003_12
Patent number
US06664255B1

Reaction notes

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