Reacción #628676

Ecuación de reacción

lithium aluminum hydride

Methyl 6-bromo-2-naphthoate

→

(6-bromonaphthalen-2-yl)methanol

Rendimiento 75.4%

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaTo a three-necked flask (5 L) cooled with an ice-bath
2. 2
   workup.ADDITIONwas added dropwise slowly through a dropping funnel
3. 3
   TemperaturaCooling bath
4. 4
   Otrowas removed
5. 5
   TemperaturaThe reaction mixture was cooled with an ice-bath again
6. 6
   workup.ADDITIONto it was added methanol (150 mL) dropwise carefully until there
7. 7
   workup.STIRRINGunder stirring for half an hour
8. 8
   OtroThe resulting solid was removed
9. 9
   Filtraciónby filtering under reduced pressure
10. 10
    Concentraciónthe filtrate was concentrated
11. 11
    workup.ADDITIONpoured into deionized water (2 L)
12. 12
    OtroThe resulting precipitate was collected by suction
13. 13
    Filtraciónfilter
14. 14
    Lavadowashed with deionized water
15. 15
    Otrodried in vacuum

Procedimiento

To a three-necked flask (5 L) cooled with an ice-bath was added lithium aluminum hydride (40 g, 1.05 mol), and anhydrous THF (500 mL) under nitrogen protection. To this suspension, Methyl 6-bromo-2-naphthoate (141 g, 0.534 mol) dissolved in anhydrous THF (1200 mL) was added dropwise slowly through a dropping funnel. Cooling bath was removed and the reaction mixture was kept under stirring for additional 2 hours. The reaction mixture was cooled with an ice-bath again, and to it was added methanol (150 mL) dropwise carefully until there was no gas release. The mixture was kept under stirring for half an hour and then was acidified with concentrated hydrochloric acid to a PH of about 4. The resulting solid was removed by filtering under reduced pressure and the filtrate was concentrated, and then poured into deionized water (2 L). The resulting precipitate was collected by suction filter, and washed with deionized water, followed by a little ethanol, and dried in vacuum to afford (6-bromonaphthalen-2-yl)methanol (95.4 g).

Fuente