Methyl iodide → Benzoic acid, 2-(methylthio)-, methyl ester

HRID 1290012Notes

Reaction equation

HRID 1290012 reaction equation
[CH3:1][O-].[Na+].[C:4]([O:13][CH3:14])(=[O:12])[C:5]1[C:6](=[CH:8][CH:9]=[CH:10][CH:11]=1)[SH:7].IC>CO>[CH3:14][O:13][C:4](=[O:12])[C:5]1[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=1[S:7][CH3:1]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 10942334Sodium Methoxide

Product 1

HCID 279586Benzoic acid, 2-(methylthio)-, methyl esterYield 388%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 160 mg (2.97 mmol) of sodium methoxide in 10 mL of methanol was added at 0°, 0.4 mL (2.97 mmol) of methyl thiosalicylate, 0.37 mL (5.97 mmol) of iodomethane and stirred at room temperature for 1 h. The reaction mixture was concentrated in vacuo, taken up in ethyl acetate, washed with water, brine, dried over sodium sulfate, and concentrated in vacuo to give 2.10 g of the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. washwashed with water, brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-94d92ca370e54d9f9a01141d8c31eb5b
Source dataset
uspto-grants-1998_05
Patent number
US05750549

Reaction notes

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