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

HRID 323445Notes

Reaction equation

HRID 323445 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-8492cfb919754d959a48db727360ba66
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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