Sodium Hydroxide → 4-(2,4-Dimethoxyphenyl)-3-methylbenzoic acid

HRID 219789Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[C:11]1[CH:16]=[CH:15][C:14]([C:17]([O:19]C)=[O:18])=[CH:13][C:12]=1[CH3:21].[OH-].[Na+]>CCO.O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[C:11]1[CH:16]=[CH:15][C:14]([C:17]([OH:19])=[O:18])=[CH:13][C:12]=1[CH3:21]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of methyl 2′,4′-dimethoxy-2-methylbiphenyl-4-carboxylate obtained in step 2 (2 g; 6.99 mmol) in EtOH (60 mL) at RT was treated with sodium hydroxide (4.19 mL; 5 M; 20.96 mmol). The reaction mixture was stirred at 60° C. for 1 hour. The reaction mixture was concentrated to give a brown solid that was taken up in water (40 mL) and the aqueous phase was washed twice with EtOAc and then acidified with HCl to pH 2. Then it was concentrated until precipitation (⅕ of the volume). The suspension was filtered off and dried under vacuum affording the title compound as an orange solid. 1H NMR (DMSO-d6, 300 MHz) δ 12.59 (br s, 1H), 7.58-7.51 (m, 2H), 6.97-6.95 (d, J=8.03 Hz, 1H), 6.81-6.79 (d, J=8.39 Hz, 1H), 6.44-6.37 (m, 2H), 3.59 (s, 3H), 3.49 (s, 3H), 1.88 (s, 3H). LC/MS (Method A): 272.9 (M+H)+; 270.9 (M−H)−. HPLC (Method A) Rt 3.87 min (Purity: 99.7%).

Workup

concentrationThe reaction mixture was concentrated
customto give a brown solid that
washthe aqueous phase was washed twice with EtOAc
concentrationThen it was concentrated until precipitation (⅕ of the volume)
filtrationThe suspension was filtered off
customdried under vacuum

Sources & evidence

ORD record: ord-dd6a45d5bdaf43c5a06709c7de8ede46
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08202865B2

Reaction notes

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