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

HRID 400756Notes

Reaction equation

HRID 400756 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%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of methyl 2,2′-dimethyl-1,1-biphenyl-4-carboxylate, prepared in Step 1 (15 g, 62.2 mmol) in THF (100 mL) was added 10% 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 HCl (3 N to 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), 7.82-7.80 (m, 1H), 7.32-7.23 (m, 3H), 7.19-7.11 (m, 1H), 7.07-7.05 (m, 1H), 2.04 (s, 3H), 1.98 (s, 3H). LC/MS (Method A): 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-3294ab385fbe46c3b9516df1e4dc6aad
Source dataset
uspto-grants-2014_06
Patent number
US08741923B2

Reaction notes

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