3-Aminobenzylalcohol synthesis
- Product Name:3-Aminobenzylalcohol
- CAS Number:1877-77-6
- Molecular formula:C7H9NO
- Molecular Weight:123.15
99-61-6
1877-77-6
GENERAL PROCEDURE: In a 10 mL round bottom flask equipped with a magnetic stirrer, m-nitrobenzaldehyde (0.123 g, 1 mmol) and water (2 mL) were added to form a mixture. Subsequently, Ni2B (0.006 g, 0.05 mmol) was added to the mixture and stirred for 5 minutes. Next, NaBH4 (0.095 g, 2.5 mmol) was added and the resulting mixture continued to be stirred for 3 minutes at room temperature. The reaction process was monitored by thin layer chromatography (TLC) using hexane/ether (5:3) as eluent. After the reaction was completed, 2% aqueous KOH solution (5 mL) was added and stirring was continued for 10 min. After that, the mixture was extracted with ethyl acetate (3 x 8 mL), the organic phases were combined and dried with anhydrous Na2SO4. Finally, the solvent was evaporated to give pure 3-aminobenzyl alcohol liquid in 95% yield (0.088 g, Table 2, entry 1).
99-61-6
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1877-77-6
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Yield:1877-77-6 97%
Reaction Conditions:
Stage #1:3-nitro-benzaldehyde with nickel boride in water at 20; for 0.0833333 h;Green chemistry;
Stage #2: with sodium tetrahydroborate in water at 20; for 0.133333 h;Green chemistry;
Steps:
A typical procedure for reduction of nitrobenzene to anilinewith NaBH4/additive Ni2B system
General procedure: In a round-bottomed flask (10 mL) equipped with a magneticstirrer, a mixture of nitrobenzene (0.123 g, 1 mmol)and H2O (2 mL) was prepared. Ni2B (0.006 g, 0.05 mmol) was then added and the mixture was stirred for 5 min.NaBH4 (0.095 g, 2.5 mmol) was also added and the resultingmixture was continued to stirring for 3 min at roomtemperature. TLC monitored the progress of the reaction(eluent, n-hexane/Et2O:5/3). After completion of the reaction,aqueous solution of KOH (2 %, 5 mL) was addedand the mixture was stirred for 10 min. The mixture wasextracted with EtOAc (3 × 8 mL) and then dried overanhydrous Na2SO4. Evaporation of the solvent affords thepure liquid aniline in 95 % yield (0.088 g, Table 2, entry 1).
References:
Zeynizadeh, Behzad;Zabihzadeh, Mehdi [Journal of the Iranian Chemical Society,2015,vol. 12,# 7,art. no. 585,p. 1221 - 1226]
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99-05-8
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24964-64-5
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1877-77-6
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