Lithium hydroxide, monohydrate → 2'-Ethyl-2-(methoxymethyl)-[1,1'-biphenyl]-4-carboxylic acid

HRID 1630972Notes

Reaction equation

HRID 1630972 reaction equation
O.[OH-].[Li+].[CH2:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[CH:17]=[CH:16][C:15]([C:18]([O:20]C)=[O:19])=[CH:14][C:13]=1[CH2:22][O:23][CH3:24])[CH3:5]>C1COCC1.O>[CH2:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[CH:17]=[CH:16][C:15]([C:18]([OH:20])=[O:19])=[CH:14][C:13]=1[CH2:22][O:23][CH3:24])[CH3:5]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 58554174Methyl 2'-ethyl-2-(methoxymethyl)-[1,1'-biphenyl]-4-carboxylate

Product 1

HCID 594958092'-Ethyl-2-(methoxymethyl)-[1,1'-biphenyl]-4-carboxylic acidYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (5.31 g, 127 mmol) was added portion-wise into a solution of methyl 2′-ethyl-2-(methoxymethyl)-1,1′-biphenyl-4-carboxylate (12.0 g, 42.2 mmol) in THF (150 mL) and water (30 mL). The resulting mixture was stirred at RT for 12 hours. The reaction mixture was concentrated under reduced pressure. The resulting aqueous layer was acidified with a concentrated aqueous solution of HCl and extracted with EtOAc. The organic layers were washed with water and brine, combined and dried (Na2SO4). The solvents were removed under reduced pressure to afford the title compound as a white solid (9.0 g, 80%). HPLC (Method A), Rt 4.2 min (purity: 96.7%). UPLC/MS, M−(ESI): 269.2. 1H NMR (DMSO-d6, 400 MHz) δ 12.9 (1H, bs), 8.08 (1H, s), 7.89 (1H, d), 7.35 (2H, m), 7.23 (2H, m), 7.04 (1H, d), 4.09 (2H, m), 3.17 (3H, s), 2.34 (1H, m), 2.22 (1H, m), 0.94 (3H, t).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionextracted with EtOAc
  3. washThe organic layers were washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. customThe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-ce27f29ecc68466ca3adc85941a6cad4
Source dataset
uspto-grants-2014_07
Patent number
US08791142B2

Reaction notes

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