Hydrochloric Acid → 4-Biphenylylacetic acid methyl ester

HRID 1594680Notes

Reaction equation

HRID 1594680 reaction equation
[C:1]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][C:4]([CH2:7][C:8]([OH:10])=[O:9])=[CH:3][CH:2]=1.Cl.[CH3:18]O>>[CH3:18][O:9][C:8](=[O:10])[CH2:7][C:4]1[CH:3]=[CH:2][C:1]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3332Felbinac

Product 1

HCID 30808634-Biphenylylacetic acid methyl esterYield 98%

Procedure

To a solution of 4-biphenylacetic acid (10 g, 47 mmol) in methanol (150 mL) was added concentrated HCl (3 mL). The mixture was heated under reflux for 16 hours, cooled to rt, and the solvent was evaporated. Chromatography of the residue over silica gel (petroleum ether followed by ethyl acetate/petroleum ether 1/4) gave 4-biphenylacetic acid methyl ester (10.4 g, 98%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 16 hours
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-89f6f13aa6804b27a5cefe72be011ca9
Source dataset
uspto-grants-2001_09
Patent number
US06284768B1

Reaction notes

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