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

HRID 542922

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].[Sb](F)(F)(F)(F)F>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 65 mg of antimony pentafluoride, and the mixture was refluxed with stirring in a water bath of 60° C. for 7 hours. During this reaction, the refluxing solvent was dried with 20 g of Molecular Sieves 3A interposed between the reaction vessel and the condenser. After completion of the reaction, a small amount of pyridine was added to the reaction solution, and the solvent was distilled off under reduced pressure. The residue was dissolved in chloroform, and the solution was washed with aqueous sodium bicarbonate and water, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to give 17.43 g (93.3%) of 1,2:3,4:5,6-tri-O-isopropylidene-D-mannitol. Melting point, 68.5°-70.5° C. (recrystallized from 70% ethanol).

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 solvent was 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 solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-a2f9b2ccf0d84d8489e8b26b34173a2b
Source dataset: uspto-grants-1987_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04659809

Linked notes

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