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

HRID 219816Notes

Reaction equation

[OH-].[Na+].C([O:6][CH2:7][C:8]1[CH:13]=[C:12]([C:14]([O:16]C)=[O:15])[CH:11]=[CH:10][C:9]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH3:24])(=O)C>CCO>[OH:6][CH2:7][C:8]1[CH:13]=[C:12]([C:14]([OH:16])=[O:15])[CH:11]=[CH:10][C:9]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH3:24]

Participants

Conditions

Temperature: 60 °C

Procedure

Sodium hydroxide (5M; 12.1 mL; 60.3 mmol; 3 eq.) was added to a solution of methyl 2-[(acetyloxy)methyl]-2′-methylbiphenyl-4-carboxylate (6 g; 20 mmol; 1 eq.) in EtOH (180 mL) and the reaction mixture was stirred at 60° C. for 2 hours. After concentration in vacuo, the residue was taken up in water (500 mL) and washed with EtOAc (2×100 mL). The aqueous phase was acidified to pH 2 with conc. HCl and extracted with EtOAc (2×100 mL). The combined organic layer was dried over MgSO4 and concentrated in vacuo to afford the title compound as a yellow solid (3.46 g, 71%). 1H NMR (DMSO-d6, 300 MHz) δ 12.97 (br s, 1H), 8.20-8.19 (m, 1H), 7.87-7.84 (dd, J=8.0 Hz, 1.86 Hz, 1H), 7.37-7.06 (m, 5H), 5.23-5.19 (m, 1H), 4.25-4.09 (m, 2H), 2.01 (s, 3H). LC/MS (Method A): 241.2 (M−H)−. HPLC (Method A) Rt 3.77 min (purity 96.1%).

Workup

concentrationAfter concentration in vacuo
washwashed with EtOAc (2×100 mL)
extractionextracted with EtOAc (2×100 mL)
dry with materialThe combined organic layer was dried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-9522520714514441a795aa73c62a9a12
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08202865B2

Reaction notes

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