I have UTFSE and get very confusing answers, if anyone could straighten this out would be appreciated.
Is it suggesting nitromethane could also be used to make
Phenylpropanolamine (2-amino-1-phenyl-1-propanol) (norpseudoephedrine)
??
As per post No 226609
(c) Method of Kamlet (3). Benzaldehyde (106 g., 1 mole) was vigorously agitated with sodium bisulfite (110 g., 1.06 mole) in 500 ml of water until the formation of the addition compound was complete. Simultaneously, nitroethane (or nitromethane) (82.5 g., 1.10 mole) was dissolved in a solution made from sodium hydroxide (45 g., 1.125 moles) dissolved in 200 ml of water. This solution was gradually added, with agitation and at room temperature, to the addition product of benzaldehyde and sodium bisulfite. After stirring for a half hour, the mixture was allowed to stand overnight. The lower layer was discarded and the upper layer was dissolved in ether and washed with sodium bisulfite solution. The ethereal solution was dried over Drierite, and after removal of ether, distilled (bp 120-130 @ 2-4 mm). The usual conversion is 90-100g. (50-55%) and the yield, based on benzaldehyde which reacts is nearly quantitative.
Preparation of 2-amino-phenyl-1-propanol. (a) With zinc and sulfuric acid. Sulfuric acid (375 g of 30% acid) was added with stiring to a mixture of 2-nitro-1-phenyl-1-propanol (54.3 g., 0.3 mole), zinc dust (90 g., 1.37 mole of 80 mesh zinc), and 100 ml of 95% ethanol. The acid was added at such a rate that the temperature remained at 45 deg C or below. Usually 10 to 12 hours were required. Agitation was continued for 1-2 hours after completing the addition of acid, then after extracting the acidic solution with ether to remove non-basic materials, a large excess of sodium hydroxide (as a 50% solution) was added. The product which was freed was extracted with ether. Three extractions, with a total of 500 ml of ether, sufficed. The ether solution was dried, ether was removed, and the product was distilled (b.p. 122 deg C at 4 to 5 mm); 29-32 g resulted (yield 65-70%). The viscous liquid solidified on standing, and m. 46-50 deg C.
According to the article, "The unmethylated amino alcohol was obtained by reduction of the nitro alcohol either with zinc and sulfuric acid, tin and hydrochloric acid, sodium amalgam and acetic acid . . . Presumably many of the ordinary metal-acid reducing agents can be used provided the temperature is kept sufficiently low to prevent dehydration."
Then A procedure wherein phenylacetone is produced from ephedrine and its derivatives with sulfuric acid, through heating with 50-70% acid at 140-155°C in the presence of 0.02-0.5% ZnCl2 as catalyst, and the formed phenylacetone is isolated from the reaction mixture by steam distillation.
What do ya think??
cheers