Reaktion #54156

Reaktionsgleichung

C6H13COCl

HCl

phenol

nitrobenzene

nitrobenzene

AlCl3

→

product

Ausbeute 82.0%

4-heptanoylphenol

Ausbeute 82.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONThere are charged to a half-liter reactor 9.4 g
2. 2
   Temperaturthe mixture is cooled below 5° C
3. 3
   workup.STIRRINGThe resulting mixture is stirred vigorously
4. 4
   workup.ADDITIONthere is added a solution of 15.5 g
5. 5
   workup.STIRRINGThe mixture is stirred at ambient temperature for 12 hours
6. 6
   workup.ADDITIONthe mixture is poured in 100 g
7. 7
   SonstigeThe organic fraction is removed by decantation
8. 8
   Waschenthe aqueous fraction is washed twice with CCl4 (100 ml.)
9. 9
   SonstigeThe organic fractions are collected
10. 10
    Waschenwashed three times with water (to neutrality)
11. 11
    SonstigeThe solvent is evaporated under reduced pressure
12. 12
    TrocknenThe organic solution is dried over anhydrous Na2SO4
13. 13
    SonstigeThe solid obtained
14. 14
    Sonstigeis recrystallized in benzene
15. 15
    SonstigeThere are obtained 16.9 g

Vorschrift

There are charged to a half-liter reactor 9.4 g. (0.1 mole) of phenol in 150 ml. of nitrobenzene. The contents of the reactor are stirred and the mixture is cooled below 5° C. Then 27 g. (0.2 mole) of AlCl3 is added in small portions over 1/2 hour. The resulting mixture is stirred vigorously and then there is added a solution of 15.5 g. of C6H13COCl (~ 0.011 mole) in 50 ml. of nitrobenzene over an hour while the temperature is kept below 5° C. The mixture is stirred at ambient temperature for 12 hours and then the mixture is poured in 100 g. of ice and 50 ml. of concentrated HCl and stirred for 1/2 hour. The organic fraction is removed by decantation and the aqueous fraction is washed twice with CCl4 (100 ml.). The organic fractions are collected and washed three times with water (to neutrality). The solvent is evaporated under reduced pressure. The organic solution is dried over anhydrous Na2SO4. The solid obtained is recrystallized in benzene. There are obtained 16.9 g. of pure product (yield 82%), melting point: 93° C.

Quelle