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

HRID 841129Notes

Reaction equation

HRID 841129 reaction equation
S([O-])([O-])(=O)=O.[Mg+2].S(=O)(=O)(O)O.[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:20]([C:25]([OH:27])=[O:26])=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:15][CH:14]=1.[CH2:28]=[C:29]([CH3:31])[CH3:30]>O.C1(C)C=CC=CC=1>[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:20]([C:25]([O:27][C:29]([CH3:31])([CH3:30])[CH3:28])=[O:26])=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 24083Sulfuric acid magnesium salt (1:1)HCID 815682-(4-Methylphenyl)benzoic acid2×

Product 1

HCID 9838270tert-Butyl 4'-methyl[1,1'-biphenyl]-2-carboxylateYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A 100-ml flask was charged with 5 ml of toluene, 0.24 g (2 mmol) of anhydrous magnesium sulfate and 0.11 ml (2 mmol) of concentrated sulfuric acid, and they were vigorously stirred. To this mixture was added 2.12 g (10 mmol) of 4′-methyl-2-biphenylcarboxylic acid, and isobutene gas (98 mmol) was introduced thereto at a flow rate of 1.2 liter/min for 2 minutes. The resulting mixture was stirred at room temperature for 6 hours. After having confirmed that almost all of the peaks ascribed to 4′-methyl-2-biphenylcarboxylic acid disappeared by HPLC, 4 ml of deionized water was poured into the mixture, and sufficiently stirred. Thereafter, the mixture was allowed to stand to separate into layers. The upper toluene layer was taken out therefrom, and the toluene layer was washed with a 1.5 M aqueous sodium hydroxide, and dried over anhydrous magnesium sulfate. Thereafter, the toluene layer was concentrated by distilling off toluene by using a rotary evaporator, to give 2.54 g of tert-butyl 4′-methyl-2-biphenylcarboxylate as crystals (yield: 95% based on 4′-methyl-2-biphenylcarboxylic acid, purity by HPLC: 99.9%).

Workup

  1. additionwas introduced
  2. stirringThe resulting mixture was stirred at room temperature for 6 hours
  3. additionwas poured into the mixture
  4. stirringsufficiently stirred
  5. customto separate into layers
  6. washthe toluene layer was washed with a 1.5 M aqueous sodium hydroxide
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationThereafter, the toluene layer was concentrated
  9. distillationby distilling off toluene
  10. customa rotary evaporator

Sources & evidence

ORD record
ord-ea67031ca34c473996d6bb8049297b71
Source dataset
uspto-grants-2002_04
Patent number
US06369266B1

Reaction notes

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