Sulfuric Acid → HCID 178521085, compound

D-Mannitol (235.6 g, 1.29 mole) is suspended in a solution of acetone (2 L) and concentrated sulfuric acid (16 ml) in a 5 L 3-neck round bottom flask equipped with a mechanical stirrer. The reaction mixture is stirred 6 hours at room temperature. The solid residue is removed by filtration (32.6 g) and the filtrate is poured into 500 ml 1.2N sodium hydroxide at 0° C. The pH of the mixture is adjusted to 7.5 with 3N sodium hydroxide (pH meter) and the acetone is removed in vacuo. The heavy aqueous slurry is chilled overnight. The solid is collected on a suction filter and the filter cake is washed well with 300 ml water. Most of the water is removed via filtration and the filter cake is dissolved in 500 ml hot 95% ethanol. The first crop of crystals forms on standing at room temperature. The crystals are filtered off, washed with 200 ml fresh cold 95% ethanol, and dried in vacuo at 25° C. to provide 121.1 g of the title compound. The mother liquor is chilled to -10° C. for 2 hours to provide a second crop of crystals which upon drying in vacuo at 25° C. provide an additional 64.9 g.

1. customequipped with a mechanical stirrer
2. customThe solid residue is removed by filtration (32.6 g)
3. additionthe filtrate is poured into 500 ml 1.2N sodium hydroxide at 0° C
4. customthe acetone is removed in vacuo
5. temperatureThe heavy aqueous slurry is chilled overnight
6. customThe solid is collected on a suction
7. filtrationfilter
8. washthe filter cake is washed well with 300 ml water
9. customMost of the water is removed via filtration
10. dissolutionthe filter cake is dissolved in 500 ml hot 95% ethanol
11. customon standing at room temperature
12. filtrationThe crystals are filtered off
13. washwashed with 200 ml fresh cold 95% ethanol
14. customdried in vacuo at 25° C.

ORD record

ord-d9643634fc264eb18cd152e31b66859c

Source dataset

uspto-grants-1992_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05116981