Hydrochloric Acid → 4-Hydroxy-4′-methoxy[1,1′-biphenyl]-3-carboxylic acid

HRID 1838784Notes

Reaction equation

HRID 1838784 reaction equation
Br[C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([OH:11])=[CH:4][CH:3]=1.[C:12](=[O:15])([O-])[O-].[Na+].[Na+].Cl>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[OH:11][C:5]1[CH:4]=[CH:3][C:2]([C:2]2[CH:10]=[CH:6][C:5]([O:15][CH3:12])=[CH:4][CH:3]=2)=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 69725-Bromosalicylic acidHCID 10340Sodium Carbonate

Product 1

HCID 51971334-Hydroxy-4′-methoxy[1,1′-biphenyl]-3-carboxylic acidYield 193.7%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×

Procedure

Palladium(II)acetate (55 mg; 0.23 mmol) was added under argon to a mixture of 5-bromosalicylic acid (5.4 g; 22.4 mmol), sodium carbonate (7.2 g; 68.1 mmol) and 4-methoxyboronic acid (3.8 g; 25 mmol) in water (125 ml). The reaction mixture was stirred at room temperature for 1 h. The resulting slurry was dissolved in hot water (1300 ml) and filtered to give a filtrate and a precipitate. The filtrate was acidified with hydrochloric acid. The precipitate was washed with water and dried in vacuo to give 5.3 g (95%) of 4-hydroxy-4′-methoxy-3-biphenylcarboxylic acid.

Workup

  1. filtrationfiltered
  2. customto give a filtrate
  3. washThe precipitate was washed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-4706609667e34cf5941bb1230742c253
Source dataset
uspto-grants-2004_01
Patent number
US06676851B1

Reaction notes

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