Sulfuric Acid → (2-Methylbutyl)benzene

HRID 1086968Notes

Reaction equation

HRID 1086968 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:10]1[CH:15]=[CH:14][CH:13]=CC=1.[Mg].OS(O)(=O)=O.[CH3:22]COCC>>[CH3:13][CH:14]([CH2:15][CH3:10])[CH2:22][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 5

HCID 1118Sulfuric AcidHCID 3283Diethyl Ether2×HCID 7961BromobenzeneHCID 5462224MagnesiumHCID 178418255HCID 178418255, compound

Product 1

HCID 107203(2-Methylbutyl)benzene

Conditions

Temperature
5 °C

Procedure

A phenylmagnesium bromide solution repapred from 40 g of bromobenzene, 6.2 g of magnesium and 300 ml of ether was cooled at 5° C., and a mixture liquid of 125 g of 2'-methylbutyl 4-methylbenzenesulfonate (II) prepared above and 130 ml of ether was added dropwise. After 2 hours of stirring, the mixture was elevated in temperature to effect 2 hours of refluxing, followed by standing overnight. To the reaction liquid, 10 % H2SO4 was added with pH 2. The organic layer was washed successively with an aqueous sodium bicarbonate solution and water, followed by drying with anhydrous magnesium sulfate, and distilling-off of the solvent. The product was distilled under reduced pressure to obtain 48 g of 4-(2'-methylbutyl)benzene (III) which showed the following IR data:

Workup

  1. additionwas added dropwise
  2. waitto effect 2 hours
  3. temperatureof refluxing
  4. waitby standing overnight
  5. additionwas added with pH 2
  6. washThe organic layer was washed successively with an aqueous sodium bicarbonate solution and water
  7. dry with materialby drying with anhydrous magnesium sulfate
  8. distillationThe product was distilled under reduced pressure

Sources & evidence

ORD record
ord-eb9d62af387c4bb59fc2ddd4ed6edb2f
Source dataset
uspto-grants-1991_07
Patent number
US05034152

Reaction notes

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