Reacción #1605809

Ecuación de reacción

Rochelle salt

lithium aluminum hydride

4-amino-5-chloro-2-methoxybenzoic acid

→

4-amino-5-chloro-2-methoxybenzyl alcohol

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added in portions under ice-water cooling
2. 2
   Temperaturathe mixture was heated
3. 3
   Temperaturaunder reflux for 5 hours
4. 4
   Otrothe reaction
5. 5
   Extracciónthe reaction mixture was extracted with ethyl acetate
6. 6
   LavadoThe organic layer was washed with a saturated aqueous solution of Rochelle salt
7. 7
   Secadoa saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
8. 8
   Concentraciónconcentrated under reduced pressure
9. 9
   OtroThe solid obtained
10. 10
    Lavadowas washed with a mixed solvent of hexane-ethyl acetate (4:1)
11. 11
    Filtracióncollected by filtration
12. 12
    Otrodried under reduced pressure

Procedimiento

To a suspension of lithium aluminum hydride (25.0 g, 116 mmol) in tetrahydrofuran (150 mL), 4-amino-5-chloro-2-methoxybenzoic acid (5 g, 28.0 mmol) was added in portions under ice-water cooling and the mixture was heated under reflux for 5 hours. Under ice-water cooling, a saturated aqueous solution of Rochelle salt was added to stop the reaction and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of Rochelle salt and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The solid obtained was washed with a mixed solvent of hexane-ethyl acetate (4:1), collected by filtration, and dried under reduced pressure to obtain 4-amino-5-chloro-2-methoxybenzyl alcohol (11.8 g)

Fuente