3-anilinopropane-1,2-diol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 83.6 g (0.5 mole) of 3-phenylamino-1,2-propanediol, 250 ml of 1,2-dimethoxyethane and 61 ml of diethyl carbonate was refluxed in a nitrogen atmosphere. Solid sodium methoxide (about 0.15 g) was added and refluxing continued for approximately 21/2 hours. The mixture was cooled, stirred with water and filtered to yield 41.1 g of 5-(hydroxymethyl)-3-phenyl-2-oxazolidinone, m.p. 122°-124° C. The 41.1 g was recrystallized from 100 ml of absolute ethanol to give 38.0 g, m.p. 125.5°-126° C. A further crop of 25.3 g (m.p. 124.5°-125° C.) was obtained from the water filtrate by concentrating and recrystallizing from ethanol. was refluxed in a nitrogen atmosphere refluxing 2 hours The mixture was cooled filtered

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 250 Grams of 40% sodium dispersion in mineral oil was added to a solution of 600 g of naphthalene in 1.8 l of 1,2-dimethoxyethane ("Glyme") stirred under nitrogen and maintained at a temperature between 20° to 30° C. After all the sodium was added, the mixture was stirred 20 minutes, and then 305 g of N-(2,3-dihydroxypropyl)-4-methyl-N-phenylbenzenesulfonamide was added through a powder addition funnel while maintaining the temperature of the reaction mixture below 35° C. After all of the solid was added, the mixture was stirred one hour. Water was then added until the color of the mixture faded from dark green or black to yellow; then concentrated hydrochloric acid was added until the solution was strongly acidic. The mixture was extracted twice with toluene and then three times with hexane, was sparged with nitrogen to remove the hexane, saturated with sodium chloride and then made basic with concentrated ammonium hydroxide. The product was extracted with dichloromethane, and the extract was dried over potassium carbonate. The filtered dichloromethane was concentrated to yield 132.3 g of 3-phenylamino-1,2-propanediol, a pale yellow oil. maintained at a temperature between 20° to 30° C the mixture was stirred 20 minutes while maintaining the temperature of the reaction mixture below 35° C After all of the solid was added the mixture was stirred one hour The mixture was extracted twice with toluene three times with hexane, was sparged with nitrogen to remove the hexane The product was extracted with dichloromethane the extract was dried over potassium carbonate The filtered dichloromethane was concentrated