Water → 3-Cyclopropoxy-2-nitrobenzoic acid

HRID 2276866Notes

Reaction equation

HRID 2276866 reaction equation
[CH:1]1([O:4][C:5]2[C:6]([N+:15]([O-:17])=[O:16])=[C:7]([CH:12]=[CH:13][CH:14]=2)[C:8]([O:10]C)=[O:9])[CH2:3][CH2:2]1.[OH-].[Li+].O>C1COCC1.CO>[CH:1]1([O:4][C:5]2[C:6]([N+:15]([O-:17])=[O:16])=[C:7]([CH:12]=[CH:13][CH:14]=2)[C:8]([OH:10])=[O:9])[CH2:2][CH2:3]1

Participants

6

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 90072167Methyl 3-cyclopropoxy-2-nitrobenzoate

Product 1

HCID 900721183-Cyclopropoxy-2-nitrobenzoic acidYield 99.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 3-cyclopropoxy-2-nitrobenzoate (4.7 g, 19.81 mmol) in THF (30 mL) and MeOH (30 mL) was treated with a solution of lithium hydroxide (2.88 g, 120 mmol) in water (15 mL, 833 mmol). The mixture was stirred at room temperature for 2 hours. The organic solvents were removed under reduced pressure. The resulting aqueous slurry was diluted with water, acidified with 1M HCl and extracted with ethyl acetate (3×). The extracts were combined and washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to provide 3-cyclopropoxy-2-nitrobenzoic acid (4.35 g, 19.8 mmol, 98% yield) as a yellowish solid. HPLC: RT=2.186 min (H2O/MeOH with TFA, SunFire C18 3.5 μm, 2.1×30 mm, gradient=4 min, wavelength=220 nm); MS(ES):m/z=246 [M+Na]+; 1H NMR (400 MHz, chloroform-d) δ 7.76 (dd, J=7.7, 1.8 Hz, 1H), 7.68-7.46 (m, 2H), 4.02 (tt, J=6.0, 2.9 Hz, 1H), 1.00-0.52 (m, 4H).

Workup

  1. customThe organic solvents were removed under reduced pressure
  2. additionThe resulting aqueous slurry was diluted with water
  3. extractionextracted with ethyl acetate (3×)
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ffb7be0f13784230a2baf63860444045
Source dataset
uspto-grants-2015_09
Patent number
US09133139B2

Reaction notes

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