Butyl iodide → a-3-Butoxy-4-iodobenzaldehyde

HRID 1361070Notes

Reaction equation

HRID 1361070 reaction equation
I[CH2:2][CH2:3][CH2:4][CH3:5].O[C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=1[I:15])[CH:10]=[O:11].C(=O)([O-])[O-:17].[K+].[K+]>C(C(C)=O)C>[CH3:2][CH2:3][CH:4]([O:11][C:10](=[O:17])[C:9]1[CH:12]=[CH:13][C:14]([I:15])=[CH:7][CH:8]=1)[CH3:5]

Participants

5

Reactant 3

HCID 10962Butyl iodideHCID 11430Potassium CarbonateHCID 27752703-Hydroxy-4-iodobenzaldehyde

Product 1

HCID 59017790a-3-Butoxy-4-iodobenzaldehyde

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
85 °C

Procedure

21.5 ml (189 mmol) of 1-iodobutane are added to a solution of 31 g (126 mmol) of 3-hydroxy-4-iodobenzaldehyde in 350 ml of methyl ethyl ketone in the presence of 52.2 g (378 mmol) 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 and 38 g (99%) of 3-butoxy-4-iodobenzaldehyde are obtained in the form of white crystals.

Workup

  1. filtrationThe solid is filtered off
  2. customthe solvent is evaporated off
  3. customThe solid obtained
  4. washis washed with heptane and 38 g (99%) of 3-butoxy-4-iodobenzaldehyde
  5. customare obtained in the form of white crystals

Sources & evidence

ORD record
ord-19ec1e0758054348959839dc5e37f8e8
Source dataset
uspto-grants-2011_02
Patent number
US07879907B2

Reaction notes

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