Water → HCID 965916, compound

HRID 1058643Notes

Reaction equation

HRID 1058643 reaction equation
[N+:1]([C:4]1[CH:11]=[C:8]([CH:9]=[O:10])[C:7]([OH:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[H-].[Na+].O>CN(C)C=O>[CH2:13]([O:12][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:11][C:8]=1[CH:9]=[O:10])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 668085-Nitrosalicylaldehyde

Product 1

HCID 965916HCID 965916, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

In an argon atmosphere, 5-nitrosalicylaldehyde (334 mg, 2.00 mmol) was dissolved in dimethyformamide (5 mL), and the solution was mixed with benzyl bromide (0.238 mL, 2.00 mmol) and sodium hydride (88 mg, 2.4 mmol), followed by stirring at 70° C. for 13 hours. The reaction solution was cooled with ice, and water was added, and then the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was triturated with diisopropyl ether to obtain 2-benzyloxy-5-nitrobenzaldehyde (337 mg, 66%).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-88e76f88c39249309458651cf8542bf6
Source dataset
uspto-grants-2003_02
Patent number
US06518268B1

Reaction notes

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