Ammonia → 3-tert-Butyltoluene

HRID 468419

反応式

HRID 468419 の反応式
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]

参加物

5

反応物 3

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

生成物 1

HCID 337113-tert-Butyltoluene収率 91.1%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-53bb1d9f6fae4ce79716c8297dccb547
出典データセット
uspto-grants-2014_01
特許番号
US08623905B2

関連ノート

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