Ethanol → 2'-Cyano-5-(methoxycarbonyl)-4'-methylbiphenyl-3-carboxylic acid
Reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:15]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[CH:13]=[C:12]([C:20]([O:22]C)=[O:21])[CH:11]=1)#[N:2].C(O)C.O1CCOCC1.[OH-].[Na+]>O>[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:15]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[CH:13]=[C:12]([C:20]([OH:22])=[O:21])[CH:11]=1)#[N:2]Participants
Procedure
A round-bottom flask was charged with dimethyl 2′-cyano-4′-methylbiphenyl-3,5-dicarboxylate (1.5 g, 4.4 mmol), ethanol (100 mL), 1,4-dioxane (20 mL), and a solution of sodium hydroxide (0.17 g, 4.4 mmol) in water (10 mL). The mixture was stirred at room temperature for 3 h. The volatiles were removed under reduced pressure, and the residue was acidified with 1N aq. HCl to pH=4 and extracted with CH2Cl2. The combined organic layers were dried and concentrated. The residue was purified via flash chromatography to afford the desired product 2′-cyano-5-(methoxycarbonyl)-4′-methylbiphenyl-3-carboxylic acid as a white solid. 1H NMR (400 MHz, DMSO-d6): 13.58 (br, 1H), 8.56 (t, J=1.3 Hz, 1H), 8.34-8.31 (m, 2H), 7.85 (s, 1H), 7.65 (d, J=2.6 Hz, 2H), 3.92 (s, 3H), 2.42 (s, 3H). 3-Ethyl 5-methyl 2′-cyano-4′-methylbiphenyl-3,5-dicarboxylate was also isolated as a white solid.
Workup
- customThe volatiles were removed under reduced pressure
- extractionextracted with CH2Cl2
- customThe combined organic layers were dried
- concentrationconcentrated
- customThe residue was purified via flash chromatography
Sources & evidence
- ORD record
- ord-d0c9f134de18464aaa9cdd9750eeb8d9
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946439B2
Reaction notes
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