Sulfuric Acid → (2-Methylbutyl)benzene

HRID 2082633Notes

Reaction equation

HRID 2082633 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:8][CH:9]([CH2:22][CH3:23])[CH2:10]OS(C1C=CC(C)=CC=1)(=O)=O.S(=O)(=O)(O)O>CCOCC>[CH3:8][CH:9]([CH2:22][CH3:23])[CH2:10][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 7961Bromobenzene2×HCID 3011991-Butanol, 2-methyl-, 1-(4-methylbenzenesulfonate)

Product 1

HCID 107203(2-Methylbutyl)benzeneYield 64.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Phenylmagnesium bromide-ether solution was prepared from bromobenzene (64.5g, 0.41m), magnesium turnings (9.85g, 0.41m), and anhydrous ether (500ml). The reagent was cooled and (+)-β-methylbutyl-4-toluenesulfonate (200g, 0.82m) in ether (800ml) was added in drops. When the addition was complete, the reaction mixture was stirred for two hours, refluxed for two hours and left to stand overnight. Aqueous sulfuric acid was added until a clear solution was formed. The layers were separated. The aqueous layer was extracted with ether (3×250ml), and the combined organic layers were washed with sodium bicarbonate solution, water and dried over anhydrous sodium sulfate. The solvent was evaporated and the residue was steam-distilled. Fractional distillation of the crude product at reduced pressure yielded (+)-β-methylbutylbenzene (38.7g, 64.8%), bp. 74°-77° C at 12 mm pressure.

Workup

  1. temperatureThe reagent was cooled
  2. additionWhen the addition
  3. temperaturerefluxed for two hours
  4. waitleft
  5. waitto stand overnight
  6. customwas formed
  7. customThe layers were separated
  8. extractionThe aqueous layer was extracted with ether (3×250ml)
  9. washthe combined organic layers were washed with sodium bicarbonate solution, water
  10. dry with materialdried over anhydrous sodium sulfate
  11. customThe solvent was evaporated
  12. distillationthe residue was steam-distilled
  13. distillationFractional distillation of the crude product at reduced pressure

Sources & evidence

ORD record
ord-e6a52b362f0e44308be25e2d6078415c
Source dataset
uspto-grants-1978_04
Patent number
US04082428

Reaction notes

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