Sulfuric Acid → (2-Methylbutyl)benzene

HRID 2082633ノート

反応式

HRID 2082633 の反応式
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

参加物

5

反応物 3

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

生成物 1

HCID 107203(2-Methylbutyl)benzene収率 64.8%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e6a52b362f0e44308be25e2d6078415c
出典データセット
uspto-grants-1978_04
特許番号
US04082428

反応ノート

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