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

HRID 572544Notes

Reaction equation

[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]([O:12]C)=[O:11])[CH:7]=[CH:6][C:5]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20].[OH-].[Na+]>CCO.O>[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]([OH:12])=[O:11])[CH:7]=[CH:6][C:5]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of methyl 2-(methoxymethyl)-2′-methylbiphenyl-4-carboxylate (40 g; 148 mmol; 1 eq.) in EtOH (1.2 L) at RT was treated with NaOH (89 mL; 5 M; 445 mmol). The reaction mixture was stirred at 60° C. for 1 hour. The reaction mixture was cooled to RT and concentrated to give a yellow solid which was taken up in water (800 mL) and the aqueous phase was washed twice with EtOAc. The aqueous phase was acidified with HCl cc (40 mL) to pH 2 and it was extracted with EtOAc (2×400 mL). The combined organics were washed with brine, dried over MgSO4 and concentrated affording the title compound as a yellow solid (35 g, 92%). 1H NMR (DMSO-d6, 300 MHz) δ 12.99 (br s, 1H), 8.09 (s, 1H), 7.92-7.89 (m, 1H), 7.33-7.22 (m, 4H), 7.10-7.08 (m, 1H), 4.11 (m, 2H), 3.18 (s, 3H), 1.99 (s, 3H). LC/MS (Method B): 255.2 (M−H)−. HPLC (Method A) Rt 4.52 min (Purity: 96.4%).

Workup

temperatureThe reaction mixture was cooled to RT
concentrationconcentrated
customto give a yellow solid which
washthe aqueous phase was washed twice with EtOAc
extractionwas extracted with EtOAc (2×400 mL)
washThe combined organics were washed with brine
dry with materialdried over MgSO4
concentrationconcentrated

Sources & evidence

ORD record: ord-329cd78f5c6743b6a0bd669dff1c1fb9
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029405B2

Reaction notes

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