Lithium Hydroxide → 3-Biphenylylacetic acid

HRID 2421637Notes

Reaction equation

HRID 2421637 reaction equation
[Li+].[OH-].C[O:4][C:5](=[O:19])[CH2:6][C:7]1[CH:8]=[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:10]=[CH:11][CH:12]=1.CO.O>CO>[C:9]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:10]=[CH:11][CH:12]=[C:7]([CH2:6][C:5]([OH:19])=[O:4])[CH:8]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 10751722Biphenyl-3-ylacetic acid methyl esterHCID 22242641Methanol--water (1/1)

Product 1

HCID 321533-Biphenylylacetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.5 mL of a 2 M LiOH solution in methanol was added to a solution of compound 91B in 3:1 MeOH/H2O solution. The reaction was stirred at room temperature for 20 hours. The mixture was concentrated under vacuum and the residue dissolved in water. 10% HCl was then added leading to a white precipitate. The solids were collected, washed thoroughly with water and dried (125 mg, 95%). NMR 1H (ppm, MeOD): 7.58 (d., J3=7.26 Hz, 2H), 7.52-7.47 (m, 2H), 7.43-7.37 (m, 3H), 7.34-7.24 (m, 2H), 3.66 (s, 2H). MS (−ESI): M−H+: 211.

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. dissolutionthe residue dissolved in water
  3. addition10% HCl was then added
  4. customThe solids were collected
  5. washwashed thoroughly with water
  6. customdried (125 mg, 95%)

Sources & evidence

ORD record
ord-d59ac40ff96c468b8bebcae95ba96b5e
Source dataset
uspto-grants-2011_06
Patent number
US07956216B2

Reaction notes

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