Pyridine → HCID 23083140, compound

HRID 2422259Notes

Reaction equation

HRID 2422259 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[CH3:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[C:12]=1[OH:18].C(=O)([O-])[O-].[K+].[K+].N1C=CC=CC=1>[Cu]=O.C1(C)C=CC=C(C)C=1>[CH3:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[C:12]=1[O:18][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6]

Participants

7

Reactant 4

HCID 1049PyridineHCID 113352,6-DimethylphenolHCID 11430Potassium CarbonateHCID 765833-Bromobenzaldehyde

Product 1

HCID 23083140HCID 23083140, compound

Reagents, catalysts & solvents 2

HCID 14829Copper oxideCatalystHCID 7929M-XyleneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 3-bromobenzaldehyde (6.1 g, 32.7 mmol), 2,6-dimethylphenol (4.0 g, 32.7 mmol), copper oxide (II) (4.4 g, 55.6 mmol), potassium carbonate (9.0 g, 65.4 mmol), pyridine (40 mL) and m-xylene (20 mL) was stirred under a nitrogen atmosphere at 140° C. for 16 hrs. The reaction mixture was cooled, the insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water. The organic layer was washed with saturated brine, dried (anhydrous sodium sulfate), and concentrated under reduced pressure to give crude 3-(2,6-dimethylphenoxy)benzaldehyde (including side product).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationthe insoluble material was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was partitioned between ethyl acetate and water
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried (anhydrous sodium sulfate)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-80f1c7c3e8ed4f9f8ca8050e93d2327d
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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