Hydrochloric Acid → 2,2'-Dimethyl-[1,1'-biphenyl]-4-carboxylic acid

HRID 2244199Notes

Reaction equation

HRID 2244199 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([O:10]C)=[O:9])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18].O1CCCC1.[OH-].[Na+].Cl>O.CO>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59606553Methyl 2,2'-dimethyl-1,1'-biphenyl-4-carboxylate

Product 1

HCID 219373032,2'-Dimethyl-[1,1'-biphenyl]-4-carboxylic acidYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 2,2′-dimethyl-1,1′-biphenyl-4-carboxylate of Step A (24.7 g, 103 mmol) in 5:1 tetrahydrofuran:methanol (200 mL) was added 1 M sodium hydroxide (108 mL, 108 mmol) and the reaction mixture was heated at reflux for 1 hour. The cooled mixture was then concentrated in vacuo to remove organic solvents. The resulting aqueous solution was cooled to 0° C. and 2 M hydrochloric acid (60 mL, 120 mmol) added slowly followed by water (60 mL) to facilitate stirring of the precipitated product. The suspension was stirred for 1 hour at 0° C. then filtered to afford the title compound (22.6 g, 97%) as a white solid, m.p. 140-143° C.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 1 hour
  3. concentrationThe cooled mixture was then concentrated in vacuo
  4. customto remove organic solvents
  5. stirringThe suspension was stirred for 1 hour at 0° C.
  6. filtrationthen filtered

Sources & evidence

ORD record
ord-f6adeed21d814ecd99e6691e79d42f00
Source dataset
uspto-grants-2010_03
Patent number
US07678787B2

Reaction notes

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