Sodium Hydroxide → 2,2'-Dimethyl-[1,1'-biphenyl]-4-carboxylic acid

HRID 2410541Notes

Reaction equation

HRID 2410541 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([O:10]C)=[O:9])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18].[OH-].[Na+]>C1COCC1>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59606553Methyl 2,2'-dimethyl-1,1'-biphenyl-4-carboxylate

Product 1

HCID 219373032,2'-Dimethyl-[1,1'-biphenyl]-4-carboxylic acidYield 95.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of methyl 2,2′-dimethyl-1,1′-biphenyl-4-carboxylate (15 g, 62.2 mmol) in THF (100 mL) was added a 10% aqueous solution of sodium hydroxide (100 mL) and the mixture was heated at 100° C. overnight. THF was removed under reduced pressure and the aqueous residue was washed with EtOAc. The aqueous layer was then acidified with a 3N aqueous solution of HCl (until pH 2-3) and extracted with DCM. The organic phase was washed with water and dried over sodium sulfate and concentrated under reduced pressure to obtain get the title compound as a white solid (13.5 g, 95%). 1H NMR (DMSO-d6, 400 MHz) δ 12.89 (bs, 1H), 7.89 (s, 1H), 7.81 (m, 1H), 7.32-7.23 (m, 3H), 7.19-7.11 (m, 1H), 7.06 (m, 1H), 2.04 (s, 3H), 1.98 (s, 3H). LC/MS (Method B): 227.0 (M+H)+. HPLC (Method B), Rt 4.1 min (purity: 99.6%).

Workup

  1. customTHF was removed under reduced pressure
  2. washthe aqueous residue was washed with EtOAc
  3. extractionextracted with DCM
  4. washThe organic phase was washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto obtain

Sources & evidence

ORD record
ord-4d24acbb42f64692a98e4a96d89ffffe
Source dataset
uspto-grants-2014_08
Patent number
US08815919B2

Reaction notes

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