Ammonia → 3-tert-Butyltoluene

HRID 468419

반응식

HRID 468419 반응식
N.P(OCC)(OCC)(O[C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:6]=1[C:12]([CH3:15])([CH3:14])[CH3:13])=O.[Li]>CCOCC>[C:12]([C:6]1[CH:5]=[CH:10][CH:9]=[C:8]([CH3:11])[CH:7]=1)([CH3:15])([CH3:14])[CH3:13]

참가 물질

5

반응물 3

HCID 222AmmoniaHCID 3028194LithiumHCID 591293942-Tert-butyl-4-methylphenyl diethyl phosphate

생성물 1

HCID 337113-tert-Butyltoluene수율 91.1%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

반응 조건

온도
-78 °C

실험 절차

To NH3 (liquid, 1000 mL) was added a solution of 2-tert-butyl-4-methylphenyl diethyl phosphate (60 g, crude from last step, about 0.2 mol) in Et2O (anhydrous, 500 mL) at −78° C. under N2 atmosphere. Lithium metal was added to the solution in small pieces until the blue color persisted. The reaction mixture was stirred at −78° C. for 15 min and then was quenched with sat. NH4Cl until the mixture turned colorless. Liquid NH3 was evaporated and the residue was dissolved in water. The mixture was extracted with Et2O (400 mL×2). The combined organics were dried over Na2SO4 and evaporated to give 1-tert-butyl-3-methylbenzene (contaminated with mineral oil) as a colorless oil (27 g, 91%), which was used directly in next step.

후처리

  1. customwas quenched with sat. NH4Cl until the mixture
  2. customLiquid NH3 was evaporated
  3. dissolutionthe residue was dissolved in water
  4. extractionThe mixture was extracted with Et2O (400 mL×2)
  5. dry with materialThe combined organics were dried over Na2SO4
  6. customevaporated

출처 및 근거

ORD 기록
ord-53bb1d9f6fae4ce79716c8297dccb547
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623905B2

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