Acetone → 1,2:3,4:5,6-Tris-O-(1-methylethylidene)hexitol

HRID 358139

Reaction equation

[CH3:1][C:2]([CH3:4])=[O:3].[CH2:5]([OH:16])[C@H:6]([C@H:8]([C@@H:10]([C@@H:12]([CH2:14]O)[OH:13])[OH:11])[OH:9])[OH:7].I>N1C=CC=CC=1>[CH3:1][C:2]1([CH3:4])[O:13][CH:12]([CH:10]2[O:11][C:6]([CH3:8])([CH3:5])[O:9][CH:8]2[CH:6]2[O:7][C:12]([CH3:14])([CH3:10])[O:16][CH2:5]2)[CH2:14][O:3]1

Participants

Conditions

Temperature: 60 °C

Procedure

To 200 ml of acetone were added 10.0 g of D-mannitol and 175 mg of hydriodic acid (57%) and the mixture was refluxed with stirring in a water bath at 60° C. for 5 hours. During this reaction, the refluxing solvent was dried with 20 g of Molecular Sieves 3A interposed between the reaction vessel and the cooling jacket. After completion of the reaction, a small amount of pyridine was added. The acetone was then distilled off under reduced pressure and the residue was dissolved in chloroform. The solution was washed with aqueous sodium bicarbonate and water and dried over anhydrous magnesium sulfate. The chloroform was distilled off under reduced pressure to give 15.0 g (90%) of 1,2:3,4:5,6-tri-O-isopropylidene-D-mannitol. After recrystallization from 70% ethanol, it melted at 68.5°-70.5° C.

Workup

temperaturethe mixture was refluxed
customDuring this reaction
dry with materialthe refluxing solvent was dried with 20 g of Molecular Sieves 3A
customAfter completion of the reaction
distillationThe acetone was then distilled off under reduced pressure
dissolutionthe residue was dissolved in chloroform
washThe solution was washed with aqueous sodium bicarbonate and water
dry with materialdried over anhydrous magnesium sulfate
distillationThe chloroform was distilled off under reduced pressure

Sources & evidence

ORD record: ord-5304b814bb924040bed5fe66f3dbb0bb
Source dataset: uspto-grants-1984_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04464530

Linked notes

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