Butyl iodide → Methyl 3-butoxy-4-iodobenzoate

HRID 250917Notes

Reaction equation

HRID 250917 reaction equation
I[CH2:2][CH2:3][CH2:4][CH3:5].[OH:6][C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][C:16]=1[I:17])[C:10]([O:12][CH3:13])=[O:11].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[CH2:2]([O:6][C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][C:16]=1[I:17])[C:10]([O:12][CH3:13])=[O:11])[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 10962Butyl iodideHCID 11430Potassium CarbonateHCID 10378812Methyl 3-hydroxy-4-iodobenzoate

Product 1

HCID 59574927Methyl 3-butoxy-4-iodobenzoateYield 99%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

In a manner similar to that of Example (25a), by reaction of 21.5 mL (0.189 mol, 1.5 eq) of 1-iodobutane and 35.03 g (0.126 mol, 1 eq) of methyl 3-hydroxy-4-iodobenzoate in 350 ml of methyl ethyl ketone in the presence of 52.24 g (0.378 mol, 3 eq) of potassium carbonate at 85° C. for 2 hours 30 minutes, and after washing with heptane, 41.78 g of methyl 3-butoxy-4-iodobenzoate are obtained in the form of white crystals. Yield=99%

Workup

  1. washafter washing with heptane, 41.78 g of methyl 3-butoxy-4-iodobenzoate
  2. customare obtained in the form of white crystals

Sources & evidence

ORD record
ord-bb3d8aca20784e3faf3ae761538c229a
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

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