Reaktion #355269

Reaktionsgleichung

p-benzyloxyaniline hydrochloride

sodium nitrite

Furfural

→

5-(p-Benzyloxyphenyl)-2-furaldehyde

Lösungsmittel

water

HCl

water

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas warmed on a steam bath for 11/2 hours
2. 2
   TemperaturThe mixture was then cooled down to 0°-5°
3. 3
   Sonstigeat 4°-7°
4. 4
   Sonstigegradually rose to 10°
5. 5
   workup.STIRRINGto stir at ambient temperature overnight
6. 6
   Sonstigeto separate after 2 days
7. 7
   workup.STIRRINGof stirring
8. 8
   SonstigeThe solid was collected
9. 9
   Waschenwashed well with water
10. 10
    workup.STIRRINGto stir for an additional 4 days while more solid
11. 11
    Sonstigeseparated
12. 12
    Sonstigetriturated with ether
13. 13
    Filtrationfiltered
14. 14
    Sonstigeair dried
15. 15
    Sonstigerecrystallizations from hot cyclohexane
16. 16
    Sonstigegave 48.5 g (17.5%)

Vorschrift

A mixture of 236 g (1.0 mole) of p-benzyloxyaniline hydrochloride in 1.5 l of water and 230 ml of conc. HCl was warmed on a steam bath for 11/2 hours. No solution was effected. The mixture was then cooled down to 0°-5° and a solution of 76 g (1.1 mole) of sodium nitrite in 500 ml of water was added in about 1 hour while keeping the temperature at 4°-7°. The mixture was allowed to stir further for an additional 45 minutes while the temperature gradually rose to 10°. Furfural (192 g, 2 moles) and 55 g of cupric chloride dihydrate in a minimum amount of water was added and the mixture was allowed to stir at ambient temperature overnight. Solid started to separate after 2 days of stirring. The solid was collected, washed well with water. The filtrate and the water washings were combined and allowed to stir for an additional 4 days while more solid separated. The dark gummy solids were combined, triturated with ether, filtered and air dried. Repeated recrystallizations from hot cyclohexane gave 48.5 g (17.5%).

Quelle