Reacción #1350612

Ecuación de reacción

3-methyl-4-nitrobenzyl alcohol

compound 89

3-methyl-4-nitrobenzyl alcohol

→

title compound

Rendimiento 99.0%

4-(hydroxymethyl)-2-methylaniline

Rendimiento 99.0%

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added in one portion
2. 2
   Otroat room temperature
3. 3
   Otrofor 1.5 hours
4. 4
   OtroThe catalyst was removed by filtration, and solvent
5. 5
   Otrowas evaporated under vacuum

Procedimiento

A solution of 3-methyl-4-nitrobenzyl alcohol (compound 89, 8.5 g, 50.9 mmol) in ethanol (100 mL) was stirred at room temperature, while 10% Pd/C (1.0 g) was added in one portion. The resulting suspension was hydrogenated (10 psi) in a Parr apparatus at room temperature for 1.5 hours. The catalyst was removed by filtration, and solvent was evaporated under vacuum to give the title compound (90, 6.9 g, 99%). MS (electrospray) 138 (M+1); 1H N MR (CDCl3) δ2.16 (s, 3H), 2.72 (br s, 3H), 4.52 (s, 2H), 6.64 (d, 1H, J=8.0 Hz), 7.02 (d, 1H, J=8.0 Hz), 7.05 (s, 1H).

Fuente