Lithium hydroxide, monohydrate → 4'-Cyano[1,1'-biphenyl]-4-carboxylic acid

HRID 265881Notes

Reaction equation

HRID 265881 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([O:17]C)=[O:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)#[N:2].O[Li].O>C1COCC1.CO.O.CCOC(C)=O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([OH:17])=[O:16])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 2764426Methyl 4-(4-cyanophenyl)benzoate

Product 1

HCID 27579544'-Cyano[1,1'-biphenyl]-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Compound 18-3 (3.4 g, 15.1 mmole), and LiOH·H2O (3.1 g, 75.5 mmol) were dissolved in THF/MeOH/H2O (30 mL/30 mL/30 mL) and stirred at room temperature overnight. The solution was diluted with EtOAc and washed with 10% KHSO4. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated to yield 18-4 as a white solid.

Workup

  1. washwashed with 10% KHSO4
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-adc7046b4d5547e6b0398afc88023ffc
Source dataset
uspto-grants-1997_07
Patent number
US05648368

Reaction notes

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