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

HRID 1725402Notes

Reaction equation

HRID 1725402 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.O.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

5

Reactant 2

HCID 2631-ButanolHCID 5870905-Fluoro-2-nitrobenzaldehyde

Product 1

HCID 112895602-(Dibutoxymethyl)-4-fluoro-1-nitrobenzeneYield 189.2%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

Dissolve 5-fluoro-2-nitrobenzaldehyde (9.43 g, 55.81 mmol), 1-butanol (12.41 g, 167.4 mmol) and 4toluenesulfonic acid monohydrate (0.9 g, 4.7 mmol) in toluene (84 mL). Heat the reaction mixture to reflux, and remove the water using a Dean-Stark apparatus. Continue to heat the reaction mixture for 3 hours. Add water and extract the aqueous layer with ethyl acetate. Combine the organic layers and dry over anhydrous sodium sulfate. Filter, concentrate under reduced pressure and purify by flash column chromatography (1% v/v triethylamine buffered silica gel, 5% ethyl acetate/hexane) to obtain 15.8 g (95%) of the title compound as colorless oil.

Workup

  1. temperatureHeat the reaction mixture
  2. temperatureto reflux
  3. customremove the water using a Dean-Stark apparatus
  4. temperatureto heat the reaction mixture for 3 hours
  5. extractionAdd water and extract the aqueous layer with ethyl acetate
  6. dry with materialdry over anhydrous sodium sulfate
  7. filtrationFilter
  8. concentrationconcentrate under reduced pressure
  9. custompurify by flash column chromatography (1% v/v triethylamine buffered silica gel, 5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8b893bda6edd4b8aa8d6110808f6c1ce
Source dataset
uspto-grants-2009_02
Patent number
US07491716B2

Reaction notes

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