M-Xylene → 5-Tert-butyl-m-xylene

HRID 1759451Notes

Reaction equation

HRID 1759451 reaction equation
[CH2:1]=[C:2]([CH3:4])[CH3:3].[C:5]1([CH3:12])[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[CH:6]=1.F.[OH-].[K+]>>[CH3:12][C:5]1[CH:10]=[C:9]([C:2]([CH3:4])([CH3:3])[CH3:1])[CH:8]=[C:7]([CH3:11])[CH:6]=1

Participants

5

Reactant 4

HCID 7929M-XyleneHCID 8255IsobutyleneHCID 14797Potassium HydroxideHCID 14917Hydrofluoric Acid

Product 1

HCID 73785-Tert-butyl-m-xylene

Procedure

1,3-Dimethyl-5-tertiary-butylbenzene is prepared as described in U.S. Pat. No. 2,860,169. According to this procedure, 448 g. (8.0 moles) of isobutene were dissolved in 961 g. (9.0 moles) of meta-xylene at 0° C. and added over a period of 4.2 hours to 150 g. (7.5 moles) of liquid hydrogen fluoride contained in a copper flask equipped with a stainless-steel stirrer, addition-tube and gas-outlet. The flask was cooled in an ice-bath. Stirring was continued for 2 hours after the end of the addition period. The contents of the flask were poured on crushed ice, neutralized with excess potassium hydroxide and the organic phase separated, washed with sodium bicarbonate solution, dried and distilled. The final product contained 17% by weight of unconverted meta-xylene, 76% of 1,3-dimethyl-5-tertiary-butylbenzene and 7% of higher boiling products.

Workup

  1. customequipped with a stainless-steel stirrer, addition-tube and gas-outlet
  2. temperatureThe flask was cooled in an ice-bath
  3. additionafter the end of the addition period
  4. additionThe contents of the flask were poured
  5. customon crushed ice
  6. customthe organic phase separated
  7. washwashed with sodium bicarbonate solution
  8. customdried
  9. distillationdistilled

Sources & evidence

ORD record
ord-34f809caf566489cb2a7a09e6cc25dc4
Source dataset
uspto-grants-1982_07
Patent number
US04340758

Reaction notes

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