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

HRID 639207Notes

Reaction equation

HRID 639207 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].[OH-].[Na+].Cl.O>O1CCCC1.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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 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 1

HCID 21899815MeOH tetrahydrofuranSolvent

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 tetrahydrofuran:methanol (5:1, 200 mL) was added 1N sodium hydroxide (108 mL, 108 mmol) and the reaction mixture was heated at reflux for 1 hour. The cooled reaction mixture was then concentrated in vacuo to remove organic solvents. The resulting aqueous solution was cooled to 0° C. and 2N hydrochloric acid (60 mL, 120 mmol) was 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. MS [(−)ESI, m/z]: 225 [M−H]−.

Workup

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

Sources & evidence

ORD record
ord-696c997dff134debbcb81c0efbbe783a
Source dataset
uspto-grants-2010_04
Patent number
US07691848B2

Reaction notes

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