Hydrochloric Acid → (biphenyl-4-yloxy)acetic acid

HRID 2269710Notes

Reaction equation

HRID 2269710 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.Br[CH2:17][C:18]([OH:20])=[O:19].Cl>O.CN(C=O)C>[C:7]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:4]([O:3][CH2:17][C:18]([OH:20])=[O:19])=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6227Bromoacetic AcidHCID 71034-HydroxybiphenylHCID 24758Sodium hydride

Product 1

HCID 262285(biphenyl-4-yloxy)acetic acidYield 65.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% dispersion in oil; 0.8 g) was added portionwise to a DMF (10 ml) solution of 4-hydroxybiphenyl (1.7 g) under ice-cooling. The reaction mixture was stirred at room temperature for 30 minutes, to which was added bromoacetic acid (1.4 g). The reaction mixture was further stirred at room temperature for 18 hours, which was poured into water. 2N hydrochloric acid was added to the mixture to adjust the pH to 4, which was extracted with ethyl acetate. The organic layer was washed with water, then dried and concentrated. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/1), and the crude crystals were recrystallized from IPE to obtain the entitled compound (1.5 g).

Workup

  1. temperaturecooling
  2. stirringThe reaction mixture was further stirred at room temperature for 18 hours
  3. extractionwas extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/1)
  8. customthe crude crystals were recrystallized from IPE

Sources & evidence

ORD record
ord-684188c482fc4c2c97acb9fa4348a47c
Source dataset
uspto-grants-2001_12
Patent number
US06329389B1

Reaction notes

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