Methanol → Methyl 4-(2-nitrophenyl)butanoate

HRID 2189031Notes

Reaction equation

HRID 2189031 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])([O-:3])=[O:2].S(Cl)(Cl)=O.[CH3:20]O>>[CH3:20][O:14][C:13](=[O:15])[CH2:12][CH2:11][CH2:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl Chloride2×HCID 2549574-(2-Nitrophenyl)butyric acid

Product 1

HCID 11401810Methyl 4-(2-nitrophenyl)butanoate

Procedure

Initially charge 705 mg (3.37 mmol) of 4-(2-nitrophenyl)butanoic acid in 7 ml of methanol, cool to 0° C. and add 0.26 ml (3.54 mmol) of thionyl chloride dropwise. Warm the mixture slowly to RT and stir overnight. To complete the reaction, add an approx. 20% excess of thionyl chloride and stir the mixture at RT for a further 5 h. After concentration under reduced pressure, stir the residue in a little methanol and filter off the resulting solid. 700 mg (95.5% of theory) of the target product are obtained as a white solid.

Workup

  1. customthe reaction
  2. stirringstir the mixture at RT for a further 5 h
  3. concentrationAfter concentration under reduced pressure
  4. stirringstir the residue in a little methanol
  5. filtrationfilter off the resulting solid
  6. custom700 mg (95.5% of theory) of the target product are obtained as a white solid

Sources & evidence

ORD record
ord-0af79bcfd4724576922441c2fa7a813b
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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