Potassium Iodide → 3-Cyclopentyloxy-4-methoxybenzaldehyde

HRID 1169847Notes

Reaction equation

HRID 1169847 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6].[I-].[K+].C(=O)([O-])[O-].[K+].[K+].[CH:20]1(Br)[CH2:24][CH2:23][CH2:22][CH2:21]1>CN(C)C=O.O>[CH:20]1([O:1][C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=2[O:10][CH3:11])[CH:5]=[O:6])[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 12127Isovanillin

Product 1

HCID 27358933-Cyclopentyloxy-4-methoxybenzaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 3-hydroxy-4-methoxy-benzaldehyde (commercially available) (1 eq) was taken in dimethylformamide (10 mL), was added potassium iodide (0.1 eq) and potassium carbonate (2 eq). The reaction mixture was stirred at 70° C. and cyclopentyl bromide (2 eq) was added dropwise. The resulting reaction mixture was stirred at 70-80° C. for 16 hours. The reaction mixture was cooled and diluted with water, extracted with ethyl acetate and washed with saturated solution of sodium chloride. The organic solvent was removed under reduced pressure. The residue thus obtained was purified by column chromatography to furnish the title compound.

Workup

  1. customThe resulting reaction mixture
  2. stirringwas stirred at 70-80° C. for 16 hours
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with ethyl acetate
  5. washwashed with saturated solution of sodium chloride
  6. customThe organic solvent was removed under reduced pressure
  7. customThe residue thus obtained
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-ead623233a6c4212ae64c7361004ca2e
Source dataset
uspto-grants-2010_11
Patent number
US07825147B2

Reaction notes

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