Butyl iodide → Methyl 3-butoxy-4-iodobenzoate

HRID 390625Notes

Reaction equation

HRID 390625 reaction equation
I[CH2:2][CH2:3][CH2:4][CH3:5].C(=O)([O-])[O-].[K+].[K+].[OH:12][C:13]1[CH:14]=[C:15]([CH:20]=[CH:21][C:22]=1[I:23])[C:16]([O:18][CH3:19])=[O:17]>C(C(C)=O)C.CCCCCCC>[CH2:2]([O:12][C:13]1[CH:14]=[C:15]([CH:20]=[CH:21][C:22]=1[I:23])[C:16]([O:18][CH3:19])=[O:17])[CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 3

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

Product 1

HCID 59574927Methyl 3-butoxy-4-iodobenzoateYield 97.3%

Reagents, catalysts & solvents 2

HCID 6569Methyl Ethyl KetoneSolventHCID 8900HeptaneSolvent

Procedure

6.15 mL (54 mmol) of iodobutane and then 14.9 g (108 mmol) of potassium carbonate are added to 10 g (36 mmol) of methyl 3-hydroxy-4-iodobenzoate in 100 mL of methyl ethyl ketone. The reaction mixture is heated at reflux for 1 hour 30 minutes. The reaction medium is filtered off and the filtrate is evaporated to dryness. The solid obtained is taken up in heptane, filtered and dried. 11.7 g (97%) of methyl 3-butoxy-4-iodobenzoate are obtained in the form of off-white crystals.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 1 hour 30 minutes
  3. filtrationThe reaction medium is filtered off
  4. customthe filtrate is evaporated to dryness
  5. customThe solid obtained
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-5aa28b274e544d55826ecfc6aa44aa4c
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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