Water → HCID 3787961, compound

HRID 2422202Notes

Reaction equation

HRID 2422202 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[C:16]1[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([O:14][C:16]2[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=2)=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 132544-PhenoxyphenolHCID 680234-Fluorobenzaldehyde

Product 1

HCID 3787961HCID 3787961, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-phenoxyphenol (1.0 g, 5.4 mmol) in N,N-dimethylformamide (20 mL) were added 4-fluorobenzaldehyde (0.67 g, 5.4 mmol) and potassium carbonate (0.75 g, 5.4 mmol), and the mixture was stirred at 100° C. for 15 hrs. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water, dried and concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=9:1) to give the title compound (1.4 μg, yield 89%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=9:1)

Sources & evidence

ORD record
ord-169880adb9f340749479712ad53b3189
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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