Water → Methyl 2-chloro-4-methoxybenzoate

HRID 1824781Notes

Reaction equation

HRID 1824781 reaction equation
O.[Cl:2][C:3]1[CH:11]=[C:10](O)[CH:9]=[CH:8][C:4]=1C(O)=O.[C:13]([O-:16])([O-])=[O:14].[K+].[K+].[CH3:19]I.O.CN([CH:25]=[O:26])C>>[CH3:19][O:16][C:13](=[O:14])[C:4]1[CH:8]=[CH:9][C:10]([O:26][CH3:25])=[CH:11][C:3]=1[Cl:2]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 533954432-Chloro-4-hydroxybenzoic acid hydrate

Product 1

HCID 13498831Methyl 2-chloro-4-methoxybenzoateYield 95%

Procedure

To 2-chloro-4-hydroxy-benzoic acid hydrate (1.1 g) in DMF (20 mL) was added K2CO3 (2.4 g) and methyl iodide (0.75 mL). After 2 h, water was added to the reaction mixture and extracted with ethyl acetate. The organic layer was washed with brine (3×) and dried over MgSO4. Flash chromatography on silica gel eluting with 10% ethyl acetate-hexane afforded 1.13 g (95%) of the title compound as an oil. MS: 201 (MH+), HPLC tR: 2.52 min.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine (3×)
  3. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-9477eedf08014b308473a9349ed66ebf
Source dataset
uspto-grants-2006_05
Patent number
US07045539B2

Reaction notes

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