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

HRID 1813870Notes

Reaction equation

HRID 1813870 reaction equation
Br[O:2][C:3]1[C:4](=[CH:8][CH:9]=[CH:10][CH:11]=1)[C:5]([OH:7])=[O:6].B([O-])([O-])O[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].Cl>O.C(OCC)(=O)C>[C:14]1([C:9]2[CH:8]=[C:4]([C:5]([OH:7])=[O:6])[C:3]([OH:2])=[CH:11][CH:10]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 19793864PhenylborateHCID 69437271Bromosalicylic acid

Product 1

HCID 675844-Hydroxy[1,1'-biphenyl]-3-carboxylic acidYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 400 ml of water, 21.7 g of bromosalicylic acid, 13.41 g of phenyl borate and 15.28 g of potassium carbonate were dissolved. The solution was stirred at room temperature for 40 minutes. The completion of the reaction was confirmed by TLC, and the reaction solution was poured into a mixture of diluted hydrochloric acid and ethyl acetate. The organic phase was extracted, separated, and washed with a saturated aqueous sodium chloride solution. The organic phase was dried with magnesium sulfate, and concentrated. The concentrate was recrystallized with acetonitrile to obtain 5-phenylsalicyclic acid as colorless crystals. The amount was 18.58 g (yield: 87%). The molecular structure was confirmed with a mass spectrum. Synthesis of ethyl 5-phenylsalicylate

Workup

  1. extractionThe organic phase was extracted
  2. customseparated
  3. washwashed with a saturated aqueous sodium chloride solution
  4. dry with materialThe organic phase was dried with magnesium sulfate
  5. concentrationconcentrated
  6. customThe concentrate was recrystallized with acetonitrile

Sources & evidence

ORD record
ord-d743137241894cd68e344ae76396d361
Source dataset
uspto-grants-2005_04
Patent number
US06875483B2

Reaction notes

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