Dimethyl Sulfate → 4-Methylbiphenyl

HRID 579924Notes

Reaction equation

HRID 579924 reaction equation
O[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.S(OC)(O[CH3:18])(=O)=O>[OH-].[Na+]>[CH3:18][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 71034-Hydroxybiphenyl

Product 1

HCID 125664-MethylbiphenylYield 89.3%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
55 °C

Procedure

In 1.5 l of a 1.5N aqueous sodium hydroxide solution was dissolved 170 g of p-hydroxybiphenyl, and 254 g of dimethyl sulfate was dropped into the content while the temperature of the content was maintained at 55° C. Reaction was carried out with stirring at 70° C. for 30 minutes. The reaction product was recovered by filtration and dried under a reduced pressure. Recrystallization of the product from ethanol yielded 150 g of 4-methylbiphenyl (melting point=75°-76° C.).

Workup

  1. additionwas dropped into the content while the temperature of the content
  2. customReaction
  3. filtrationThe reaction product was recovered by filtration
  4. customdried under a reduced pressure
  5. customRecrystallization of the product from ethanol

Sources & evidence

ORD record
ord-657a642f6f0d4c3abafdfe624fc611f0
Source dataset
uspto-grants-1988_06
Patent number
US04751018

Reaction notes

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