Methyl iodide → Methyl 4-chloro-2-hydroxybenzoate

HRID 590616Notes

Reaction equation

HRID 590616 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=[O:7].[C:12]([O-])([O-])=O.[Cs+].[Cs+].CI>CN(C=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:12])=[O:7])=[C:4]([OH:11])[CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 787824-Chlorosalicylic acid

Product 1

HCID 327085Methyl 4-chloro-2-hydroxybenzoateYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-chlorosalicylic acid (75 g, 435.6 mmol) in anhydrous DMF (871 mL) was added Cs2CO3 (70.7 g, 217.8 mmol) and MeI (27.5 mL, 439.9 mmol) sequentially. The reaction mixture was stirred at room temperature overnight. Ice cold water (3 L) was added to the reaction mixture and the precipitated solid was filtered and dried to provide VII-1-I (75 g, 92% yield).

Workup

  1. filtrationthe precipitated solid was filtered
  2. customdried
  3. customto provide VII-1-I (75 g, 92% yield)

Sources & evidence

ORD record
ord-14db83a364054151a6e16f63ccbe5ebd
Source dataset
uspto-grants-2016_01
Patent number
US09233983B2

Reaction notes

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