Sodium Hydroxide → 2'-(Methoxymethyl)-2-methylbiphenyl-4-carboxylic acid

HRID 219833Notes

Reaction equation

[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([O:18]C)=[O:17])=[CH:12][C:11]=1[CH3:20].[OH-].[Na+]>CCO.O>[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([OH:18])=[O:17])=[CH:12][C:11]=1[CH3:20]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of methyl 2′-(methoxymethyl)-2-methylbiphenyl-4-carboxylate (3 g; 11.10 mmol; 1 eq.) in EtOH (90 mL) at RT was treated with NaOH (6.66 mL; 5 M; 33.29 mmol; 3 eq.). The reaction mixture was stirred at 60° C. for 2 hours. The reaction mixture was concentrated to give a brown solid which was taken up in water (100 mL) and the aqueous phase was washed twice with EtOAc. The aqueous phase was acidified with HCl cc to pH 2 and it was extracted with EtOAc. The combined organics were washed with brine, dried over MgSO4 and concentrated affording the title compound as a beige solid. 1H NMR (DMSO-d6, 300 MHz) δ 12.95 (br s, 1H), 7.92-7.91 (m, 1H), 7.84-7.81 (dd, J=7.83 Hz, 1.91 Hz, 1H), 7.55-7.52 (m, 1H), 7.47-7.38 (m, 2H), 7.25-7.22 (d, J=7.86 Hz, 1H), 7.15-7.14 (m, 1H), 4.09 (m, 2H), 3.17 (s, 3H), 2.07 (s, 3H). LC/MS (Method B): 255.2 (M−H)−. HPLC (Method A) Rt 4.35 min (Purity: 96.8%).

Workup

concentrationThe reaction mixture was concentrated
customto give a brown solid which
washthe aqueous phase was washed twice with EtOAc
extractionwas extracted with EtOAc
washThe combined organics were washed with brine
dry with materialdried over MgSO4
concentrationconcentrated

Sources & evidence

ORD record: ord-1b4201ac260646d8a01960d379e5cf12
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08202865B2

Reaction notes

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