Sodium Hydroxide → 4'-Butyl[1,1'-biphenyl]-4-carboxylic acid

HRID 1464902Notes

Reaction equation

HRID 1464902 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17]C)=[O:16])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+]>C1COCC1.O>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[CH:13][C:14]([C:15]([OH:17])=[O:16])=[CH:19][CH:20]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 1782412HCID 1782412, compound

Product 1

HCID 27573044'-Butyl[1,1'-biphenyl]-4-carboxylic acidYield 71.1%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A mixture of methyl 4-(4-butylphenyl)benzoate (89.0 g, 0.332 mol), NaOH (26.6 g, 0.664 mol) in THF/H2O (500 mL/100 mL) was heated to reflux overnight. After TLC showed the reaction was complete, THF was removed. The residue was adjusted pH ˜3-4 with 2 N HCl solution. The resulting mixture was filtered and the cake was washed with water, dried to give 4-(4-butylphenyl)benzoic acid (60.0 g, yield: 71.1%), as a white solid. (ESI) m/z 255.0 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customTHF was removed
  4. filtrationThe resulting mixture was filtered
  5. washthe cake was washed with water
  6. customdried

Sources & evidence

ORD record
ord-c0c1a7ec171f462c96ac11ac2c6c6c67
Source dataset
uspto-grants-2015_04
Patent number
US08999922B2

Reaction notes

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