Lithium Hydroxide → 2'-Cyano-5-(hydroxymethyl)-4'-methylbiphenyl-3-carboxylic acid

HRID 1845302Notes

Reaction equation

HRID 1845302 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:15]=[C:14]([CH2:16][OH:17])[CH:13]=[C:12]([C:18]([O:20]C)=[O:19])[CH:11]=1)#[N:2].[OH-].[Li+].[NH4+].[Cl-].CCOC(C)=O>O1CCOCC1.O>[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:15]=[C:14]([CH2:16][OH:17])[CH:13]=[C:12]([C:18]([OH:20])=[O:19])[CH:11]=1)#[N:2]

Participants

7

Reactant 4

HCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 58187956Methyl 2'-cyano-5-(hydroxymethyl)-4'-methylbiphenyl-3-carboxylate

Product 1

HCID 581883422'-Cyano-5-(hydroxymethyl)-4'-methylbiphenyl-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of methyl 2′-cyano-5-(hydroxymethyl)-4′-methylbiphenyl-3-carboxylate (220 mg, 0.78 mmol) in 1,4-dioxane (5 mL) and water (1 mL) was added lithium hydroxide (60 mg, 2.5 mmol). The reaction mixture was stirred at rt for 8 h, and then treated with aq. NH4Cl and EtOAc. The organic layer was separated, dried over anhydrous MgSO4, and concentrated. The residue was purified by silica gel chromatography to afford the title compound. 1H NMR (acetone-d6, 400 MHz): 8.16 (m, 1H), 8.11 (m, 1H), 7.81 (m, 1H), 7.73 (m, 1H), 7.65-7.61 (m, 1H), 7.56 (d, 1H, J=8.0 Hz), 4.81 (s, 2H), 2.46 (s, 3H).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over anhydrous MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-05c5e1b0124749b193f10313bf558961
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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