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

HRID 1642615Notes

Reaction equation

HRID 1642615 reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].[C:12]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C.CCOC(C)=O>[CH3:11][O:10][C:1](=[O:9])[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[S:4][CH3:12]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 21009Benzoic acid, 2-mercapto-, methyl ester

Product 1

HCID 279586Benzoic acid, 2-(methylthio)-, methyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl thiosalicylate (4.0 g, 23.8 mmol) in DMF (25 mL) is added K2CO3 (4.0 g, 28.94 mmol) followed by methyl iodide (2.3 mL, 36.9 mmol). The resulting mixture is stirred at ambient temperature for 1 h. The mixture is diluted with EtOAc and washed with 1N HCl (3×) and water (1×). The organic phase is dried over MgSO4, filtered and concentrated to afford 2-methylsulfanylbenzoic acid methyl ester.

Workup

  1. washwashed with 1N HCl (3×) and water (1×)
  2. dry with materialThe organic phase is dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f4db0d847db548438334ed4912af000c
Source dataset
uspto-grants-2012_02
Patent number
US08119666B2

Reaction notes

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