Dimethyl Sulfate → Methyl 2-chloro-4-methoxybenzoate

HRID 1363414Notes

Reaction equation

HRID 1363414 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:5]=1[Cl:11].[H-].[Na+].S(OC)(O[CH3:19])(=O)=O>O1CCOCC1>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:19])=[CH:6][C:5]=1[Cl:11]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 134988302-Chloro-4-hydroxy-benzoic acid methyl ester

Product 1

HCID 13498831Methyl 2-chloro-4-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
62.5 °C

Procedure

To a solution of compound of example 163 (2.8 g, 15 mmol) in dry dioxane (50 mL) was added NaH (50%, 1.44 g, 30 mmol) and dimethyl sulfate (3.78 g, 30 mmol). It was stirred at 60-65° C. for 1 h. It was poured into ice water and extracted with EtOAc (2×100 mL). The organic extract was washed with brine, dried (anhydrous Na2SO4) and concentrated to obtain the title compound.

Workup

  1. extractionextracted with EtOAc (2×100 mL)
  2. extractionThe organic extract
  3. washwas washed with brine
  4. dry with materialdried (anhydrous Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9137fee05f894d7990cfd4273956aa17
Source dataset
uspto-grants-2011_02
Patent number
US07884127B2

Reaction notes

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