4-Hydroxybenzaldehyde → HCID 54893623, compound

HRID 547613Notes

Reaction equation

HRID 547613 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.F[C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[C:13]([CH3:20])[CH:12]=1.C([O-])([O-])=O.[K+].[K+]>CN(C)C=O.C(OC(=O)C)C>[CH3:20][C:13]1[CH:12]=[C:11]([O:1][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)[CH:16]=[CH:15][C:14]=1[N+:17]([O-:19])=[O:18]

Participants

6

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 949565-Fluoro-2-nitrotoluene

Product 1

HCID 54893623HCID 54893623, compoundYield 104.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Hydroxybenzaldehyde (945 mg, 7.7 mmol), 4-fluoro-2-methyl-1-nitrobenzene (1.0 g, 6.4 mmol), and K2CO3 (1.77 g, 12.8 mmol) were stirred in 55 mL dimethylformamide at 100 degrees Centigrade for 18 hours. The reaction was cooled to room temperature, diluted with ethylacetate, extracted two times with 1N NaOH, and rinsed with brine. The organic layer was dried over MgSO4, filtered and concentrated to afford 1.72 g crude 4-[(3-methyl-4-nitrophenyl)oxy]benzaldehyde, which was used without further purification.

Workup

  1. extractionextracted two times with 1N NaOH
  2. washrinsed with brine
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-60d9335a37a446f692712dd700cf9931
Source dataset
uspto-grants-2011_05
Patent number
US07939528B2

Reaction notes

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