Water → tert-Butyl 4'-methyl[1,1'-biphenyl]-2-carboxylate

HRID 841132Notes

Reaction equation

HRID 841132 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([OH:16])=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.O.[CH2:18]=[C:19]([CH3:21])[CH3:20].O=P(Cl)(Cl)Cl.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([O:16][C:19]([CH3:21])([CH3:20])[CH3:18])=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 962WaterHCID 8255IsobutyleneHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 815682-(4-Methylphenyl)benzoic acid

Product 1

HCID 9838270tert-Butyl 4'-methyl[1,1'-biphenyl]-2-carboxylateYield 95.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 500-ml flask was charged with 50 ml of toluene and 53.42 g (0.25 mol) of 4′-methyl-2-biphenylcarboxylic acid, 0.45 ml (0.025 mol) of water and 32.63 g (0.58 mol) of isobutene. To this mixture was added dropwise 7.74 g (0.05 mol) of phosphorus oxytrichloride, and the mixture was stirred for 6 hours. The reaction mixture was added to 50 ml of a 10%-aqueous sodium hydroxide and washed. The organic layer was dried over anhydrous magnesium sulfate. Thereafter, the organic layer was concentrated by distilling off toluene by using a rotary evaporator, to give 64.2 g of tert-butyl 4′-methyl-2-biphenylcarboxylate as crystals (yield: 95% based on 4′-methyl-2-biphenylcarboxylic acid, purity by HPLC: 99.9%). Incidentally, the obtained compound had the same physical properties as those of the compound obtained in Example II-1.

Workup

  1. washwashed
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationThereafter, the organic layer was concentrated
  4. distillationby distilling off toluene
  5. customa rotary evaporator

Sources & evidence

ORD record
ord-6ec4bd531d3840cc9bddfb117ceba82e
Source dataset
uspto-grants-2002_04
Patent number
US06369266B1

Reaction notes

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