Lithium Hydroxide → 4-(2,6-Dimethylphenyl)benzoic acid

HRID 2244212Notes

Reaction equation

HRID 2244212 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:18])=[CH:7][CH:6]=1)=[O:4].[OH-].[Li+]>O1CCCC1>[CH3:18][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]([CH3:17])[C:11]=1[C:8]1[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68690855HCID 68690855, compound

Product 1

HCID 219372914-(2,6-Dimethylphenyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2′,6′-dimethyl-1,1′-biphenyl-4-carboxylic acid methyl ester (5 g, 20.8 mmol) in tetrahydrofuran (70 mL) was treated dropwise under nitrogen with 1 N lithium hydroxide (45 mL). The mixture was heated at reflux for 8 hours, filtered warm (Celite) and concentrated in vacuo to remove organic solvents. The aqueous residue was acidified in the cold to pH 3 with 2N hydrochloric acid. The precipitate was collected, washed with water ad dried. The residue was dissolved in ethyl acetate, treated with charcoal (with warming), filtered (Celite) and evaporated to yield the title compound as an off-white crystalline solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 8 hours
  3. filtrationfiltered
  4. temperaturewarm (Celite)
  5. concentrationconcentrated in vacuo
  6. customto remove organic solvents
  7. customThe precipitate was collected
  8. washwashed with water ad
  9. customdried
  10. dissolutionThe residue was dissolved in ethyl acetate
  11. additiontreated with charcoal (with warming)
  12. filtrationfiltered (Celite)
  13. customevaporated

Sources & evidence

ORD record
ord-10f3d4f7659845ff9209d22d96c85389
Source dataset
uspto-grants-2010_03
Patent number
US07678787B2

Reaction notes

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