Hydrochloric Acid → 4-Biphenylylacetic acid methyl ester

HRID 1387292Notes

Reaction equation

HRID 1387292 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-d2a8faec8cdb4e2785435497ae8ba8bf
Source dataset
uspto-grants-2001_07
Patent number
US06268365B1

Reaction notes

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