Hydrogen Bromide → alpha-Methyl-4'-(hydroxy)[1,1'-biphenyl]-4-acetic acid

HRID 1587582Notes

Reaction equation

HRID 1587582 reaction equation
[CH3:1][CH:2]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)[C:3]([O:5]CC)=[O:4].Br>C(O)(=O)C>[CH3:1][CH:2]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[CH:16][C:17]([OH:20])=[CH:18][CH:19]=2)=[CH:10][CH:9]=1)[C:3]([OH:5])=[O:4]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 86746941alpha-Methyl-4'-(methoxy)[1,1'-biphenyl]-4-acetic acid, ethyl ester

Product 1

HCID 18956586alpha-Methyl-4'-(hydroxy)[1,1'-biphenyl]-4-acetic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture containing α-methyl-4'-(methoxy)[1,1'-biphenyl]-4-acetic acid, ethyl ester (22.0 g, 77.4 mmol), acetic acid (400 mL) and 48% hydrobromic acid (80 mL) is refluxed for 18 hours. The solution is concentrated under reduced pressure to one-third the volume and the product crystallizes from the solution. The solid is filtered and dried to give a quantitative yield. A portion of this material is recrystallized from acetonitrile and a white solid is obtained, m.p. 205°-206° C. MS (EI m/z): 242 (M)+, (b.p., M-CO2H)+.

Workup

  1. temperatureis refluxed for 18 hours
  2. concentrationThe solution is concentrated under reduced pressure to one-third the volume
  3. customthe product crystallizes from the solution
  4. filtrationThe solid is filtered
  5. customdried
  6. customto give a quantitative yield
  7. customA portion of this material is recrystallized from acetonitrile
  8. customa white solid is obtained

Sources & evidence

ORD record
ord-3ada4222d9394696a76220b1121831a0
Source dataset
uspto-grants-1993_06
Patent number
US05218124

Reaction notes

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