Methanol → 4-Methyl[1,1'-biphenyl]-2-carboxylic acid

HRID 1477740Notes

Reaction equation

HRID 1477740 reaction equation
[OH-:1].[Na+].[CH3:3][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][C:5]=1C(OC)=O.[CH3:20][OH:21]>>[CH3:3][C:4]1[CH:5]=[C:6]([C:20]([OH:21])=[O:1])[C:7]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 18388812HCID 18388812, compound

Product 1

HCID 189334774-Methyl[1,1'-biphenyl]-2-carboxylic acid

Conditions

Temperature
65 °C

Procedure

32% aq. NaOH (74 mL) was added to a rt solution of methyl 4-methyl-[1,1′-biphenyl]-3-carboxylate (15.5 g, 0.068 mol) in MeOH (124 mL). The rxn mixture was stirred at 65° C. for 2 h, then the org. solvent was evaporated, water added, and the aq. layer acidified with conc. HCl. The mixture was stirred at rt for 30 min, and the precipitate was filtered off to give the title compound A-1-14 as a white solid. LC-MS A: tR=0.80 min; [M+H]+=no ionization.

Workup

  1. customsolvent was evaporated
  2. additionwater added
  3. stirringThe mixture was stirred at rt for 30 min
  4. filtrationthe precipitate was filtered off

Sources & evidence

ORD record
ord-16efbfcc56a1437da86647056beefc48
Source dataset
uspto-grants-2016_08
Patent number
US09403813B2

Reaction notes

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