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

HRID 557209Notes

Reaction equation

HRID 557209 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 4-toluenesulfonic 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-59d1b837d3ca4318ad8e71d363b1fed1
Source dataset
uspto-grants-2011_11
Patent number
US08058425B2

Reaction notes

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