Synthesis of 1-Phenyl-2-nitropropanol [6343-57-3]

1-Phenyl-2-nitropropanol [6343-57-3-A]            C9H11NO3

Procedure according to U.S. Patent 2,151,517 from Sittig, Marshall - Pharmaceutical Manufacturing Encyclopedia (2nd Edition), page 1220

In a solution of 11 kg of sodium bisulfite in 50 l of water, add 10.7 kg of technical benzaldehyde and stir vigorously. Once the disulfite formation is complete, add a solution of 8.25 kg of nitroethane and 4.5 kg of sodium hydroxide in 20 l of water. The added solution should still be warm. Stir the resulting white reaction mixture vigorously for 30 minutes and then let it stand overnight.
The product settles as the upper phase. This phase is separated and stirred vigorously with a solution of 11 kg of sodium bisulfite in 50 l of water for 15 minutes, the product is now free of aldehyde and is separated from the supernatant solution and filtered. The bisulfite solution from the last step can be reused in the first step of the preparation. Between 17.1 and 17.7 kg of 1-Phenyl-2-nitropropanol is obtained.

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Last updated: 26/08/2007

(1R,2S)-1-Phenyl-2-nitropropanol [503441-17-6-A]            C9H11NO3

10.2 g (0.132 mol) of nitroethane and 17.1 g (0.169 mol) of triethylamine are thoroughly mixed and cooled to -8 °C. Then, 5.1 g (0.047 mol) of benzaldehyde is added and stirred for 162 minutes at -10 °C. The reaction mixture is then neutralized. The solution is extracted with MTBE. The ether is washed 3-4 times with 5 ml of sodium bisulfite solution (5 g in 20 ml) and then 2 times with concentrated NaCl solution. The ether is dried and distilled off. 7.52 g (88% of the theoretical yield) of a slightly yellowish product is obtained. The product is characterized by its high content of the 1R,2S-isomer.

Source: Rhodium Archive with own additions
Delivered by: Kanonenfutter
Last updated: 26/08/2007

Other names: alpha-(1-Nitroethyl)-benzyl alcohol; alpha-(1-Nitroethyl)-benzyl methanol; 2-Nitro-1-phenyl-1-propanol; NSC 16258