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

HRID 2246844Notes

Reaction equation

HRID 2246844 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 aqueous sodium hydroxide (108 mL, 108 mmol). The reaction mixture heated at reflux for 1 hour, cooled and then concentrated in vacuo to remove organic solvents. The resulting aqueous solution was cooled to 0° C. and 2 M aqueous 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 h at 0° C. then filtered to afford the title compound (22.6 g) as a white solid, m. p. 140-143° C.

Workup

  1. temperatureThe reaction mixture heated
  2. temperatureat reflux for 1 hour
  3. temperaturecooled
  4. concentrationconcentrated in vacuo
  5. customto remove organic solvents
  6. stirringThe suspension was stirred for 1 h at 0° C.
  7. filtrationthen filtered

Sources & evidence

ORD record
ord-6736c45eeee0419f93b9d09c1c4d200b
Source dataset
uspto-grants-2010_03
Patent number
US07687623B2

Reaction notes

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