Lithium Hydroxide → 2-Ethoxy-2'-methyl-[1,1'-biphenyl]-4-carboxylic acid

HRID 2410536Notes

Reaction equation

HRID 2410536 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[C:8]([C:10]([O:12]C)=[O:11])[CH:7]=[CH:6][C:5]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20])[CH3:2].[OH-].[Li+]>C1COCC1.O>[CH2:1]([O:3][C:4]1[CH:9]=[C:8]([C:10]([OH:12])=[O:11])[CH:7]=[CH:6][C:5]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20])[CH3:2]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 58554138Methyl 2-ethoxy-2'-methyl-[1,1'-biphenyl]-4-carboxylate

Product 1

HCID 580663802-Ethoxy-2'-methyl-[1,1'-biphenyl]-4-carboxylic acidYield 93.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 2-ethoxy-2′-methyl-1,1′-biphenyl-4-carboxylate (11 g, 40.6 mmol) in a mixture of THF (100 mL) and water (10 mL) was added lithium hydroxide (6.82 g, 162.7 mmol) in portions. After 24 hours at RT, the reaction mixture was evaporated and the residue was taken up with water. The aqueous layer was acidified with a concentrated aqueous solution of HCl and extracted with EtOAc. The organic layer was washed with brine, dried (Na2SO4) and concentrated under vacuum affording of the title compound as pale yellow solid (9.7 g, 93%). LC/MS (Method B): 255.0 (M−H)−. 1H-NMR (DMSO-d6, 400 MHz) δ 13.02 (br s, 1H), 7.57 (m, 2H), 7.18-7.25 (m, 4H), 7.09 (d, 1H), 4.05 (q, 2H), 2.05 (s, 3H), 1.18 (t, 3H).

Workup

  1. customthe reaction mixture was evaporated
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-bf7c1b4750334942ad443f34ec0638e2
Source dataset
uspto-grants-2014_08
Patent number
US08815919B2

Reaction notes

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