Potassium Carbonate → 4-[3-(Allyloxy)phenoxy]benzaldehyde

HRID 1370831Notes

Reaction equation

HRID 1370831 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1)[CH:2]=[CH2:3].C([O-])([O-])=O.[K+].[K+].F[C:19]1[CH:26]=[CH:25][C:22]([CH:23]=[O:24])=[CH:21][CH:20]=1>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][CH:10]=1)[O:11][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=[O:24])=[CH:21][CH:20]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 680234-FluorobenzaldehydeHCID 53141523-(Allyloxy)phenol

Product 1

HCID 185123024-[3-(Allyloxy)phenoxy]benzaldehydeYield 60%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

The crude product from Example 61B in anhydrous DMF (40 mL) was treated with K2CO3 (15.5 g, 112 mmoles) and 4-fluorobenzaldehyde (4.82 mL, 44.9 mmoles). The reaction mixture was stirred overnight at 100° C. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate. The mixture was washed with H2O (2×), brine, dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, 8% ethyl acetate:hexanes) to provide the title compound (5.75 g, 60%).

Workup

  1. temperatureAfter cooling to room temperature
  2. washThe mixture was washed with H2O (2×), brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure
  6. customThe residue was purified by flash chromatography (silica gel, 8% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-f00f316953c0490bb1351c39a64d504a
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

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