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

HRID 841131Notes

Reaction equation

HRID 841131 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=P(Cl)(Cl)Cl.[CH2:22]=[C:23]([CH3:25])[CH3:24]>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:23]([CH3:25])([CH3:24])[CH3:22])=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8255IsobutyleneHCID 24813Phosphorus oxychlorideHCID 815682-(4-Methylphenyl)benzoic acid2×

Product 1

HCID 9838270tert-Butyl 4'-methyl[1,1'-biphenyl]-2-carboxylateYield 98%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 100-ml flask was charged with 5 ml of toluene and 2.12 g (10 mmol) of 4′-methyl-2-biphenylcarboxylic acid, and they were vigorously stirred. To this mixture was added dropwise 0.18 ml (2 mmol) of phosphorus oxytrichloride, and isobutene gas (98 mmol) was introduced to the mixture 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, the reaction solution was washed with a 1.5 M aqueous sodium hydroxide. The reaction solution was dried over anhydrous magnesium sulfate, and then the mixture was concentrated by distilling off toluene by using a rotary evaporator, to give 2.63 g of tert-butyl 4′-methyl-2-biphenylcarboxylate as crystals (yield: 98% 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. additionwas introduced to the mixture at a flow rate of 1.2 liter/min for 2 minutes
  2. stirringThe resulting mixture was stirred at room temperature for 6 hours
  3. washthe reaction solution was washed with a 1.5 M aqueous sodium hydroxide
  4. dry with materialThe reaction solution was dried over anhydrous magnesium sulfate
  5. concentrationthe mixture was concentrated
  6. distillationby distilling off toluene
  7. customa rotary evaporator

Sources & evidence

ORD record
ord-e942e7c7b8474daa9b9623a1f72faffa
Source dataset
uspto-grants-2002_04
Patent number
US06369266B1

Reaction notes

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