Nitric Acid → Methyl 4-cyclobutyl-3-nitrobenzoate

HRID 541447Notes

Reaction equation

HRID 541447 reaction equation
[CH:1]1([C:5]2[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=2)[CH2:4][CH2:3][CH2:2]1.[N+:15]([O-])([OH:17])=[O:16].O>C(OC(=O)C)(=O)C>[CH:1]1([C:5]2[CH:6]=[CH:7][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:13][C:14]=2[N+:15]([O-:17])=[O:16])[CH2:2][CH2:3][CH2:4]1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 68288440Methyl 4-cyclobutylbenzoate2×

Product 1

HCID 68288364Methyl 4-cyclobutyl-3-nitrobenzoateYield 64%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
30 °C

Procedure

To a solution of methyl 4-cyclobutylbenzoate (compound 168.1, 3.80 g, 20.0 mmol, 1.00 equiv) in acetic anhydride (12 mL) 0° C. was added dropwise fuming HNO3 (5 mL, 97%). The resulting mixture was stirred at 30° C. in an oil bath. After 2 h, 30 mL of water was carefully added and the mixture was extracted with 2×30 mL of ethyl acetate. The combined organic layers were washed with aqueous saturated NaHCO3 (note: gas evolution), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified using silica gel column chromatography with ethyl acetate/petroleum ether (1:25) as eluent to furnish 3.00 g (64%) of the title compound as a light yellow oil.

Workup

  1. extractionthe mixture was extracted with 2×30 mL of ethyl acetate
  2. washThe combined organic layers were washed with aqueous saturated NaHCO3 (note: gas evolution)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified

Sources & evidence

ORD record
ord-25ea02c8bfdf4a07b63e3fe5f82bd070
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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