1-t-Butylazo-1-chlorocyclohexane → 1-t-Butylazo-1-phenylcyclohexane

HRID 436361

Reaktionsgleichung

Reaktionsgleichung von HRID 436361
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:9]([N:13]=[N:14][C:15]1(Cl)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)([CH3:12])([CH3:11])[CH3:10]>CCOCC>[C:9]([N:13]=[N:14][C:15]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)([CH3:12])([CH3:11])[CH3:10]

Komponenten

4

Edukt 2

HCID 233447841-t-Butylazo-1-chlorocyclohexaneHCID 178418255HCID 178418255, Verbindung

Produkt 1

HCID 202888901-t-Butylazo-1-phenylcyclohexane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

To a clean, dry 250 ml. round bottom + neck flask equipped with a magnetic stirrer, thermometer, condenser and addition funnel, which was being purged with nitrogen, was added an ether solution containing .06 moles of phenylmagnesium bromide. The solution was cooled to 5° C. and a solution of 8.7 g. (.043 moles) of 1-t-butylazo-1-chlorocyclohexane in 50 ml. of ether was added dropwise over 1/2 hour. After the addition was complete, the reaction was stirred for 15 minutes at room temperature and the excess phenylmagnesium bromide destroyed by the addition of wet ether. The reaction mixture was poured into 200 ml. of cold water and the ether layer separated, washed with 5% HCl, saturated sodium bicarbonate solution, saturated sodium chloride solution, dired over anhydrous sodium sulfate, filtered and the ether removed on a rotating evaporator leaving 9.75 g. (93%) of a yellow liquid. The infrared spectrum of the product was in agreement with the structure of the title compound.

Aufarbeitung

  1. customTo a clean, dry 250 ml
  2. customround bottom + neck flask equipped with a magnetic stirrer
  3. additionthermometer, condenser and addition funnel
  4. customwhich was being purged with nitrogen
  5. additionwas added an ether solution
  6. additionAfter the addition
  7. customthe excess phenylmagnesium bromide destroyed by the addition of wet ether
  8. additionThe reaction mixture was poured into 200 ml
  9. customof cold water and the ether layer separated
  10. washwashed with 5% HCl, saturated sodium bicarbonate solution, saturated sodium chloride solution
  11. filtrationfiltered
  12. customthe ether removed on a rotating evaporator
  13. customleaving 9.75 g

Quellen und Nachweise

ORD-Eintrag
ord-5cfba88e039b4ff29c7484247454ecae
Quelldatensatz
uspto-grants-1977_02
Patentnummer
US04008273

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