Water → Methyl 3-butoxy-4-iodobenzoate

HRID 1951972Notes

Reaction equation

HRID 1951972 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+].O>CC(=O)CC>[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

6

Reactant 4

HCID 962WaterHCID 10962Butyl iodideHCID 11430Potassium CarbonateHCID 10378812Methyl 3-hydroxy-4-iodobenzoate

Product 1

HCID 59574927Methyl 3-butoxy-4-iodobenzoateYield 49.5%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
60 °C

Procedure

14.7 ml (130 mmol) of iodobutane is added to a solution of 30 g (110 mmol) of methyl 3-hydroxy-4-iodobenzoate and 17.9 g (130 mmol) of potassium carbonate in 300 ml of 2-butanone. The reaction mixture is heated at 60° C. for 16 hours. After adding 100 ml of water and then extraction with ethyl acetate, the organic phases are combined, dried over sodium sulfate, and filtered. The solvents are evaporated and then the residue is taken up in heptane and filtered. 18.2 g of methyl 3-butoxy-4-iodobenzoate is obtained in the form of white crystals. The filtrate is concentrated and the residue is purified by silica column chromatography, eluted with a heptane/ethyl acetate mixture 8/2, obtaining 11.6 g of methyl 3-butoxy-4-iodobenzoate. 29.8 g (82%) of methyl 3-butoxy-4-iodobenzoate is thus obtained.

Workup

  1. extractionextraction with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customThe solvents are evaporated
  5. filtrationfiltered

Sources & evidence

ORD record
ord-bb7ff20a6bc540f9863ee46fb9ae91b4
Source dataset
uspto-grants-2013_03
Patent number
US08404836B2

Reaction notes

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