Phenol → 2-Nitro-5-phenoxybenzaldehyde

HRID 390208Notes

Reaction equation

HRID 390208 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH:7]=[O:8].[C:13]1([OH:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O.CCCCCC>[N+:10]([C:5]1[CH:4]=[CH:3][C:2]([O:19][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:9][C:6]=1[CH:7]=[O:8])([O-:12])=[O:11]

Participants

7

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 5870905-Fluoro-2-nitrobenzaldehyde

Product 1

HCID 442030822-Nitro-5-phenoxybenzaldehyde

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5-fluoro-2-nitrobenzaldehyde (15.00 g, 0.089 mol), phenol (9.12 g, 0.098 mol), and K2CO3 (13.5 g, 0.089 mol) in 200 mL of DMF was heated at 120° C. for 50 min. The reaction mixture was cooled and concentrated in vacuo. To the residue was added EtOAc (500 mL) and H2O (500 mL). The layers were separated, and the EtOAc extract was concentrated. The residue was purified on silica gel using 20% EtOAc-hexane as eluent. The product containing fractions were combined and concentrated to yield a yellow oil which solidified on standing. This material was dissolved in a minimal quantity of EtOAc and hexane, and the resulting solution was cooled in a dry ice acetone bath. Filtration yielded 2-nitro-5-phenoxy-benzaldehyde as a light yellow solid. The filtrate was concentrated in vacuo to yield additional 2-nitro-5-phenoxy-benzaldehyde.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated in vacuo
  3. additionTo the residue was added EtOAc (500 mL) and H2O (500 mL)
  4. customThe layers were separated
  5. extractionthe EtOAc extract
  6. concentrationwas concentrated
  7. customThe residue was purified on silica gel using 20% EtOAc-hexane as eluent
  8. additionThe product containing fractions
  9. concentrationconcentrated
  10. customto yield a yellow oil which
  11. temperaturethe resulting solution was cooled in a dry ice acetone bath
  12. filtrationFiltration

Sources & evidence

ORD record
ord-0a2736780b214673a916a05ce48aa6d6
Source dataset
uspto-grants-2013_02
Patent number
US08383637B2

Reaction notes

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