Methyl 5-(chloromethyl)-2-methoxybenzoate → Methyl 2-methoxy-5-(methylthiomethyl)benzoate

HRID 637178Notes

Reaction equation

HRID 637178 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([CH2:13]Cl)=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].[CH3:15][S-:16].[Na+]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([CH2:13][S:16][CH3:15])=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 2

HCID 240622Methyl 5-(chloromethyl)-2-methoxybenzoateHCID 4378561Sodium methanethiolate

Product 1

HCID 18464711Methyl 2-methoxy-5-(methylthiomethyl)benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

Combine methyl 2-methoxy-5-chloromethylbenzoate (5 mmol) and dimethylformamide (10 mL). Cool in an ice bath and add sodium thiomethoxide (15 mmol). Heat to 75° C. After 5.5 hours, partition the reaction mixture between water and ethyl acetate. Extract the organic layer with water, dry over Na2SO4, filter, and concentrate in vacuo to give methyl 2-methoxy-5-(methylthiomethyl)benzoate.

Workup

  1. temperatureCool in an ice bath
  2. custompartition the reaction mixture between water and ethyl acetate
  3. extractionExtract the organic layer with water
  4. dry with materialdry over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-72a46de999e94018b4e5febf840cd229
Source dataset
uspto-grants-2001_02
Patent number
US06194406B1

Reaction notes

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