Ammonia → 3-tert-Butyltoluene

HRID 1403991

Reaktionsgleichung

Reaktionsgleichung von HRID 1403991
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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 337113-tert-ButyltolueneAusbeute 91,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-7a6eed558178463ab27e4aebda1b6c29
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08912199B2

Verknüpfte Notizen

Wird geladen…