Iodoethane → Methyl 3-ethoxy-4-methoxybenzoate

HRID 1934723Notes

Reaction equation

HRID 1934723 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[K+].[K+].[CH2:20](I)[CH3:21]>CN(C)C=O>[CH2:20]([O:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6])[CH3:21]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 4056967Methyl 3-hydroxy-4-methoxybenzoate

Product 1

HCID 10536413Methyl 3-ethoxy-4-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of methyl 3-hydroxy-4-methoxybenzoate (4.00 g) and potassium carbonate (4.55 g) in dimethylformamide (20 mL) was added ethyl iodide (2.63 mL) under water-cooling and the mixture was stirred for 2 hours at ambient temperature. The mixture was partitioned between water and ethyl acetate. The separated organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo to give methyl 3-ethoxy-4-methoxybenzoate as pale brown powders (4.55 g).

Workup

  1. temperaturecooling
  2. customThe mixture was partitioned between water and ethyl acetate
  3. washThe separated organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-74d2c9a455b34eb781fbbe8965161b48
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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