HCID 23436447, compound → 2-(3,3-Dimethylbutynyl)-4-nitrobenzoic Acid
Reaction equation
[CH3:1][C:2]([CH3:19])([CH3:18])[C:3]#[C:4][C:5]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:6]=1[C:7]([O:9]C)=[O:8]>CO>[CH3:1][C:2]([CH3:19])([CH3:18])[C:3]#[C:4][C:5]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:6]=1[C:7]([OH:9])=[O:8]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
Methyl 2-(3,3-dimethylbutynyl)-4-nitrobenzoate (0.8 g, 3.1 phenol) was dissolved in 50 mL of methanol containing 5% potassium hydroxide solution and the reaction was stirred at room temperature for 2 hours. The reaction mixture was concentrated and the residue was taken up in water and washed with diethyl ether. The aqueous fraction was carefully acidified with concentrated HCl to a pH of 2.0 and extracted with ethyl acetate (2×50 mLs). The organic fractions were combined, washed once with a saturated solution of sodium chloride, dried over magnesium sulfate and concentrated to give the title compound (0.7 g, 91%) an off-white solid: m.p. 170-173° (C.); 1H NMR (300 MHz, methanol-d4) δ 8.16 (d, J=2.2 Hz, 1H, Aromatic), 8.12 (dd, J=8.7, 2.3 Hz, 1H, Aromatic), 7.96 (d, J=8.5 Hz, 1H, Aromatic), 1.35 (s, 9H, t-Butyl); 13C NMR (75 MHz, methanol-d4) δ 168.5, 150.7, 140.4, 132.4, 129.0, 126.6, 123.1, 107.4, 77.7, 31.2, 29.6; MS m/e calc'd for: 247.0845, found 247.0821.
Workup
- concentrationThe reaction mixture was concentrated
- washwashed with diethyl ether
- extractionextracted with ethyl acetate (2×50 mLs)
- washwashed once with a saturated solution of sodium chloride
- dry with materialdried over magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-3df30e9d6bc44c039e92ca0ac8039149
- Source dataset
- uspto-grants-2004_02
- Patent number
- US06693123B2
Reaction notes
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