Pyridine → 4-(4-Isopropoxyphenoxy)benzaldehyde

HRID 404879Notes

Reaction equation

HRID 404879 reaction equation
[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)([CH3:3])[CH3:2].Br[C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+].N1C=CC=CC=1>[O-2].[Cu+2].ClCCl>[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C:13]2[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 1049PyridineHCID 11430Potassium CarbonateHCID 707414-BromobenzaldehydeHCID 820014-Isopropoxyphenol

Product 1

HCID 877217474-(4-Isopropoxyphenoxy)benzaldehydeYield 56.2%

Reagents, catalysts & solvents 2

HCID 164827Copper oxide (CuO)CatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of Example 17A (1.50 g, 9.86 mmol), 4-bromobenzaldehyde (2.20 g, 11.9 mmol.), (K2CO3 (2.85 g, 20.6 mmol) and pyridine (50 mL) at 80° C. was added Cu(II) oxide (1.95 g, 24.5 mmol). After the addition, the mixture was refluxed vigorously for 20 hours. After cooling, dichloromethane was added and the mixture was filtered through Celite. The filtrate was concentrated to dryness. The residue was dissolved in ether, which was washed with 10% HCl (2×), 1N NaOH (2×), brine (1×), dried over MgSO4, and concentrated to dryness. The residue was purified on silica gel eluting with a hexane and ethyl acetate gradient to give the desired product as a white solid (1.42 g, 56%).

Workup

  1. additionAfter the addition
  2. temperaturethe mixture was refluxed vigorously for 20 hours
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered through Celite
  5. concentrationThe filtrate was concentrated to dryness
  6. dissolutionThe residue was dissolved in ether
  7. washwhich was washed with 10% HCl (2×), 1N NaOH (2×), brine (1×)
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated to dryness
  10. customThe residue was purified on silica gel eluting with a hexane and ethyl acetate gradient

Sources & evidence

ORD record
ord-d9dd6c9633f04085bc54f055c08be427
Source dataset
uspto-grants-2014_06
Patent number
US08748627B2

Reaction notes

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