Iodoethane → Methyl 4-ethoxy-3-methoxybenzoate

HRID 612119Notes

Reaction equation

HRID 612119 reaction equation
[C:1]([O:12][CH3:13])(=[O:11])[C:2]1[CH:10]=[CH:9][C:7]([OH:8])=[C:4]([O:5][CH3:6])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:20](I)[CH3:21]>CN(C=O)C>[CH2:20]([O:8][C:7]1[CH:9]=[CH:10][C:2]([C:1]([O:12][CH3:13])=[O:11])=[CH:3][C:4]=1[O:5][CH3:6])[CH3:21]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 19844Methyl Vanillate

Product 1

HCID 592192Methyl 4-ethoxy-3-methoxybenzoateYield 89.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 25.0 g (137 mmol) methyl vanillate, 38.87 g (274 mmol) potassium carbonate, 500 ml DMF, and 16.5 ml (206 mmol) ethyl iodide was heated to 100° C. under N2. At 2.5 hours, cooled and removed solids. Stripped solvent, and partitioned between water and methylene chloride. Stripped solvent and dried in vacuo, giving 25.85 g of white solid: mass spectrum (EI m/e): M=210.0.

Workup

  1. temperaturecooled
  2. customremoved solids
  3. customStripped solvent, and partitioned between water and methylene chloride
  4. customdried in vacuo

Sources & evidence

ORD record
ord-32b0b8b26aaf4d6fb2720a564ed87758
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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