Isopropyl iodide → 5-chloro-2-isopropoxybenzaldehyde

HRID 1728164Notes

Reaction equation

HRID 1728164 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].I[CH:12]([CH3:14])[CH3:13].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH:12]([CH3:14])[CH3:13])=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 124815-Chloro-salicylaldehyde

Product 1

HCID 51996155-chloro-2-isopropoxybenzaldehydeYield 78.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Chloro-2-hydroxy-benzaldehyde (3 g, 19.16 mmol),2-Iodo-propane (4.88 g, 28.74 mmol) and K2CO3 (4 g, 28.74 mmol) was mixed in anhydrous DMF. The reaction tube was placed into the cavity of a focused monomode microwave reactor and the contents of the flask were irradiated for 30 min at 100° C. Then the solution was filtered and the filtration was concentrated to obtain the crude product (3 g). The crude product was used into next step reaction without further purification.

Workup

  1. customThe reaction tube was placed into the cavity of a focused monomode microwave reactor
  2. customthe contents of the flask were irradiated for 30 min at 100° C
  3. filtrationThen the solution was filtered
  4. filtrationthe filtration
  5. concentrationwas concentrated

Sources & evidence

ORD record
ord-831fe5f47a49478886682d089bd99e2a
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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