Water → 1-(2-Methoxy-5-nitrophenyl)ethanol

HRID 1861975Notes

Reaction equation

HRID 1861975 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:4]=1[CH:5]=[O:6].[CH3:14][Al](C)C.O>C1(C)C=CC=CC=1.CCCCCC>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:4]=1[CH:5]([OH:6])[CH3:14]

Participants

6

Reactant 3

HCID 962WaterHCID 90685Benzaldehyde, 2-methoxy-5-nitro-HCID 16682925Trimethylaluminum

Product 1

HCID 186220311-(2-Methoxy-5-nitrophenyl)ethanolYield 79%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

To a solution of 2-methoxy-5-nitrobenzaldehyde (450 mg) in toluene (30 ml), a solution of trimethylaluminum in hexane (3.0 ml) was added dropwise under ice cooling. After stirring at room temperature for 1 h, water was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed successively with water and a saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=2:1) to give 385 mg of the titled compound (yield, 79%).

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed successively with water
  3. dry with materiala saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-cdfd5856939e4e309cf7f12bb653f4fc
Source dataset
uspto-grants-2003_03
Patent number
US06534546B1

Reaction notes

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