Sodium Hydroxide → 4-(2-Methoxyphenyl)-3-methylbenzoic acid
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]([O:17]C)=[O:16])=[CH:11][C:10]=1[CH3:19].[OH-].[Na+]>CCO.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]([OH:17])=[O:16])=[CH:11][C:10]=1[CH3:19]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
To solution of methyl 2′-methoxy-2-methylbiphenyl-4-carboxylate, prepared in Step 1 (2 g; 7.80 mmol; 1 eq.) in EtOH (60 mL), was added at RT an aqueous solution of sodium hydroxide (4.68 mL; 5 M; 23.41 mmol; 3 eq.). The reaction mixture was stirred at 60° C. for one hour. The reaction mixture was concentrated under vacuum to give an orange solid. It was taken up in water (400 mL) and the aqueous phase was washed twice with EtOAc (200 mL). Aqueous phase was acidified with concentrated HCl (2 mL) to pH 2. Then it was concentrated under vacuum until a precipitate was formed. (⅕ of volume). The suspension was filtered off and dried under vacuum to afford the title compound as a brown solid. 1H NMR: (DMSO-d6, 300 MHz) δ 12.89 (s, 1H), 7.86 (s, 1H), 7.82-7.79 (dd, J=7.99 Hz, J=1.23 Hz, 1H), 7.46-7.40 (m, 1H), 7.26-7.23 (d, J=7.68 Hz, 1H), 7.16-7.04 (m, 3H), 3.75 (s, 3H), 2.13 (s, 3H). LC/MS (Method A): 240.9 (M−H)−. HPLC (Method A) Rt 4.05 min (Purity: 98.5%).
Workup
- concentrationThe reaction mixture was concentrated under vacuum
- customto give an orange solid
- washthe aqueous phase was washed twice with EtOAc (200 mL)
- concentrationThen it was concentrated under vacuum until a precipitate
- customwas formed
- filtrationThe suspension was filtered off
- customdried under vacuum
Sources & evidence
- ORD record
- ord-bb9479d6b27e4faba0cd02bcd86f8223
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08202865B2
Reaction notes
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