Iodoethane → Methyl 3-chloro-4-ethoxybenzoate

HRID 2189737Notes

Reaction equation

HRID 2189737 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([Cl:11])[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:19](I)[CH3:20]>CN(C=O)C>[Cl:11][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=1[O:10][CH2:19][CH3:20])[C:3]([O:2][CH3:1])=[O:12]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 77580Methyl 3-chloro-4-hydroxybenzoate

Product 1

HCID 20110212Methyl 3-chloro-4-ethoxybenzoateYield 97.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Methyl-4-hydroxy-3-chlorobenzoate (10 g, 53.6 mmol) and potassium carbonate (14.8 g, 107.2 mmol) were suspended in DMF (110 ml) and then ethyl iodide (8.56 ml, 107.2 mmol) was added. The reaction mixture was heated to 70° C. overnight. The reaction mixture was filtered and the residue washed with ether. The organic solutions were evaporated in vacuo and then dissolved in EtOAc and washed with aq. NaOH and water, dried and evaporated to dryness in vacuo to afford the title compound (11.24 g) as a yellow oil. MS (ES): C10H1135ClO3 requires 214; found (MH+) 215.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe residue washed with ether
  3. customThe organic solutions were evaporated in vacuo
  4. dissolutiondissolved in EtOAc
  5. washwashed with aq. NaOH and water
  6. customdried
  7. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-20c773ef15b542c387966d26e79c49aa
Source dataset
uspto-grants-2012_12
Patent number
US08324254B2

Reaction notes

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