2-Nitro (CAS NO.: ), which is also known as Ethanol, 2-nitro-, could be produced through the following synthetic routes.

In a 5-l., three-necked, round-bottomed flask fitted with a 30-ml. dropping funnel, mechanical stirrer, and thermometer extending down into the liquid is placed a suspension of paraformaldehyde (trioxymethylene, 125 g., 4.16 moles) in freshly distilled nitromethane (2.5 l., 46.6 moles). The suspension is stirred vigorously, and 3N methanolic potassium hydroxide solution is added dropwise from the dropping funnel until, at an apparent pH of 6–8, but closer to pH 8 (pH paper), the paraformaldehyde begins to dissolve and the suspension assumes a clearer appearance. About 10 ml. of the alkaline solution is required, and the addition takes about 10 minutes. About 15–20 minutes after addition of the alkaline solution is complete, the paraformaldehyde dissolves completely. Shortly thereafter, the solution temperature reaches a maximum of 13–14 degrees above room temperature and then slowly drops. Stirring is continued 1 hour after addition of the alkaline solution is complete.

Stirring is continued while the added alkali is completely neutralized by adding concentrated (36N) sulfuric acid (1 ml.) dropwise from a medicine dropper over a period of about 3 minutes until an apparent pH of about 4 is reached. The solution is then stirred for an hour, during which time the pH should not change.

The precipitated potassium sulfate is filtered by passing the solution through a 12-cm. Büchner funnel. The light-yellow or yellowish green filtrate is transferred to a 5-l., one-necked, round-bottomed flask fitted with a Claisen head containing a capillary ebulliator tube and a thermometer, and connected to a water-cooled condenser. The condenser is connected through a vacuum adapter to a 3-l., one-necked, round-bottomed flask, cooled in ice, to act as a receiver. About 2.3 l. of pure, unchanged nitromethane is removed by distillation at aspirator pressure and a water-bath temperature of 40–50°. The distillation takes about 6–7 hours.

The golden-yellow residue (315–365 g.) is transferred to a 1-l., one-necked, round-bottomed flask containing an equal weight of diphenyl ether. The flask is fitted with a Claisen head containing a capillary ebulliator tube and a thermometer, and connected to a water-cooled condenser. The condenser is connected to a 3- or 4-port fraction cutter fitted with 100–500 ml., one-necked, round-bottomed flasks, at least one of which is 500 ml. or larger to accommodate the main fraction. The mixture is distilled under the vacuum of a good pump. The fore-run, b.p. 29–33° at about 0.10 mm., consisting of nitromethane (about 56 ml.), can be distilled at a water-bath temperature of 32–79° and usually passes directly into the Dry Ice trap protecting the vacuum pump. The temperature then rises as 2-nitroethanol and diphenyl ether codistil. The main fraction, a two-phase distillate initially richer in 2-nitroethanol than diphenyl ether, gradually changes in composition until the proportion of 2-nitroethanol becomes negligible. The main fraction of 410–425 g., b.p. 54–57° at about 0.10 mm. (or 64–66° at about 0.4 mm.), collects at a water-bath temperature of 79–88°. Care should be taken to prevent clogging of the condenser or fraction cutter with solid diphenyl ether (m.p. 27°). The distillation is continued until the proportion of 2-nitroethanol (lower layer) observed in the distillate becomes negligible, and the temperature suddenly starts to rise. At this point heating is stopped, but the residue is cooled to room temperature or below before the vacuum is broken.

The two-phase main fraction of the distillate is placed in a 500-ml. separatory funnel and the lower layer of crude 2-nitroethanol (185–200 g., 146–158 ml., n²⁵D 1.4493–1.4513, containing about 92–94 mole % 2-nitroethanol) is drawn off. The 2-nitroethanol is then extracted in a 500-ml. separatory funnel with an equal volume of light petroleum ether (b.p. 60–68°, such as Skellysolve B) or hexane, and the colorless lower layer of 2-nitroethanol (174–188 g., 46–49%, n²⁵D 1.4432–1.4433, containing about 98 mole % 2-nitroethanol) is drawn off. The product turns light yellow after standing for a day or more.