1-Butanol → HCID 17985768, compound

HRID 751484Notes

Reaction equation

HRID 751484 reaction equation
[CH3:1][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.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:1]([O:8][CH:7]([O:17][CH2:13][CH2:14][CH2:15][CH3:16])[C:6]1[CH:9]=[C:2]([CH3:1])[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 118051105-Methyl-2-nitrobenzaldehyde

Product 1

HCID 17985768HCID 17985768, compoundYield 199.5%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

Dissolve 5-methyl-2-nitrobenzaldehyde (7.84 g, 47.52 mmol), 1-butanol (10.55 g, 142.6 mmol) and toluene-4-sulfonic acid (0.5 g) in toluene (200 mL). Heat to reflux, and remove the water using a Dean-Stark apparatus. Heat for 3 hours. Add water, and extract the aqueous layer with ethyl acetate. Combine the organic layers, dry over sodium sulfate, filter, concentrate under reduced pressure, and purify by flash chromatography (1% v/v triethylamine buffered silica gel, 5% ethyl acetate/hexane) to give 14 g (99%) of the title compound as colorless oil.

Workup

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

Sources & evidence

ORD record
ord-36303ee89a4145879646aa7f46552f44
Source dataset
uspto-grants-2008_07
Patent number
US07405305B2

Reaction notes

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