Methyl Ethyl Ketone → Methyl 3-butoxy-4-iodobenzoate

HRID 1092290Notes

Reaction equation

HRID 1092290 reaction equation
[I:1]CCCC.[OH:6][C:7]1(I)[CH:16]=[CH:15][CH:14]=[C:9]([C:10]([O:12][CH3:13])=[O:11])[CH2:8]1.C(=O)([O-])[O-].[K+].[K+].[CH2:24]([C:26]([CH3:28])=O)[CH3:25]>>[CH2:25]([O:6][C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][C:16]=1[I:1])[C:10]([O:12][CH3:13])=[O:11])[CH2:24][CH2:26][CH3:28]

Participants

5

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 10962Butyl iodideHCID 11430Potassium CarbonateHCID 66590855Methyl 3-hydroxy-3-iodobenzoate

Product 1

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

Conditions

Temperature
85 °C

Procedure

21.5 mL (0.189 mol, 1.5 eq) of 1-iodobutane are added to a solution of 35.03 g (0.126 mol, 1 eq) of methyl 3-hydroxy-3-iodobenzoate in 350 ml of methyl ethyl ketone in the presence of 52.24 g (0.378 mol, 3 eq) of potassium carbonate. The reaction medium is heated at 85° C. for 2 hours. The solid is filtered off and the solvent is evaporated off. The solid obtained is washed with heptane to give 41.78 g of methyl 3-butoxy-4-iodobenzoate in the form of white crystals. Yield=99%.

Workup

  1. filtrationThe solid is filtered off
  2. customthe solvent is evaporated off
  3. customThe solid obtained
  4. washis washed with heptane

Sources & evidence

ORD record
ord-c34359ad455040f5b1dfe1c616447d63
Source dataset
uspto-grants-2012_03
Patent number
US08129416B2

Reaction notes

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