1-Butanol → 2-(Dibutoxymethyl)-4-fluoro-1-nitrobenzene

HRID 240246Notes

Reaction equation

HRID 240246 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH2:13]([OH:17])[CH2:14][CH2:15][CH3:16]>C1(C)C=CC=CC=1.C(OCC)(=O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:3]([O:8][CH:7]([O:17][CH2:13][CH2:14][CH2:15][CH3:16])[C:6]1[CH:9]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[N+:10]([O-:12])=[O:11])[CH2:2][CH2:9][CH3:6]

Participants

6

Reactant 2

HCID 2631-ButanolHCID 5870905-Fluoro-2-nitrobenzaldehyde

Product 1

HCID 112895602-(Dibutoxymethyl)-4-fluoro-1-nitrobenzeneYield 192%

Reagents, catalysts & solvents 3

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Heat a solution of 5-fluoro-2-nitro-benzaldehyde (10 g, 59.17 mmol), butanol (20 mL, 219 mmol) and p-toluenesulfonic acid (600 mg, 3.15 mmol) in toluene (200 mL) at reflux for 2 hours in a flask equipped with a Dean-Stark trap. Cool the reaction mixture to room temperature, dilute with ethyl acetate (400 mL), and wash sequentially with saturated aqueous sodium bicarbonate (300 mL×3) and saturated aqueous sodium chloride (300 mL×2). Dry the organic phase over sodium sulfate and concentrate under reduced pressure to provide the desired compound as a pale yellow oil (17 g, 96%).

Workup

  1. temperatureat reflux for 2 hours in a flask
  2. customequipped with a Dean-Stark trap
  3. washwash sequentially with saturated aqueous sodium bicarbonate (300 mL×3) and saturated aqueous sodium chloride (300 mL×2)
  4. dry with materialDry the organic phase over sodium sulfate
  5. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-902c81d93d414c2c9eccdc1acb407da5
Source dataset
uspto-grants-2014_02
Patent number
US08648063B2

Reaction notes

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