Sodium Hydroxide → 4-Isopropyl-2-nitrobenzoic acid
Reaction equation
[CH:1]([C:4]1[CH:11]=[CH:10]C(C#N)=[C:6]([N+:12]([O-:14])=[O:13])[CH:5]=1)([CH3:3])[CH3:2].[OH-].[Na+].O.[C:18]([OH:21])(=[O:20])[CH3:19]>>[CH:1]([C:4]1[CH:11]=[CH:10][C:19]([C:18]([OH:21])=[O:20])=[C:6]([N+:12]([O-:14])=[O:13])[CH:5]=1)([CH3:3])[CH3:2]Participants
Procedure
The product of Example 431B (1.746 g, 9.1798 mmol) dissolved in a 2:1:1 v/v/v mixture of water/acetic acid/concentrated sulfuric acid (24 mL) was heated at reflux for 3 days. The reaction was cooled, poured onto ice water (80 mL) and adjusted to pH12 with 6N aqueous sodium hydroxide. The reaction was washed with ethyl ether (3×50 mL). The aqueous phase was acidified to pH 2 with concentrated hydrochloric acid and extracted with ethyl ether (2×75 mL). The ethereal extracts were dried over magnesium sulfate, filtered, and concentrated by rotary evaporation. The residue was co-concentrated with methylene chloride (5 mL)/hexanes (100 mL) three times and dried on high vacuum to afford the title compound as an off-white solid (1.402 g, 6.702 mmol, 73%). 1H NMR (300 MHz, DMSO-D6) δ ppm 1.23 (d, J=6.62 Hz, 6 H) 2.88-3.23 (m, 1 H) 7.66 (dd, J=8.09, 1.84 Hz, 1 H) 7.80 (d, J=7.72 Hz, 1 H) 7.83 (d, J=1.47 Hz, 1 H) 13.70 (br s, 1 H).
Workup
- temperaturewas heated
- temperatureat reflux for 3 days
- temperatureThe reaction was cooled
- additionpoured onto ice water (80 mL)
- washThe reaction was washed with ethyl ether (3×50 mL)
- extractionextracted with ethyl ether (2×75 mL)
- dry with materialThe ethereal extracts were dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated by rotary evaporation
- customdried on high vacuum
Sources & evidence
- ORD record
- ord-eec7f62a86d549d58b1d6ca6bb1051ed
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07910595B2
Reaction notes
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