4-Hydroxybenzaldehyde → 4-(4-Nitrophenoxy)benzaldehyde

HRID 2066088Notes

Reaction equation

HRID 2066088 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1.O>CN(C=O)C>[N+:23]([C:20]1[CH:21]=[CH:22][C:17]([O:1][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)=[CH:18][CH:19]=1)([O-:25])=[O:24]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 11430Potassium CarbonateHCID 114661-Bromo-4-nitrobenzene

Product 1

HCID 47395914-(4-Nitrophenoxy)benzaldehydeYield 82.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-hydroxybenzaldehyde (366 mg, 3 mmol) in anhydrous DMF (7 ml), under nitrogen atmosphere, K2CO3 (829 mg, 6 mmol), and, after 10 minutes, 4-bromonitrobenzene (726 mg, 3.6 mmol) were added. The mixture was heated to reflux for 3 hours, then water was added and the product was extracted with CH2Cl2. The organic layers were washed with water and with NaCl saturated solution and dried with Na2SO4. After evaporation of the solvent the crude product was purified by chromatography on silica gel (Petroleum ether/Ethyl acetate 5/1); 605 mg (yield 82%) of pure title product were obtained.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 hours
  3. extractionthe product was extracted with CH2Cl2
  4. washThe organic layers were washed with water and with NaCl saturated solution
  5. dry with materialdried with Na2SO4
  6. customAfter evaporation of the solvent the crude product
  7. customwas purified by chromatography on silica gel (Petroleum ether/Ethyl acetate 5/1)

Sources & evidence

ORD record
ord-41b58b9b2d874b8990990f3500ff7cdc
Source dataset
uspto-grants-2012_10
Patent number
US08288528B2

Reaction notes

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