Mannitol → 1,2:5,6-Di-O-isopropylidene-D-mannitol

HRID 1648831Notes

Reaction equation

HRID 1648831 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].[CH2:17](O)[C@H:18]([C@H:20]([C@@H]([C@@H](CO)O)O)O)O>[Cl-].[Zn+2].[Cl-].CC(C)=O>[CH3:1][C:2]1([CH3:4])[O:13][C@@H:12]([C@@H:10]([OH:11])[C@H:8]([OH:9])[C@@H:6]2[O:7][C:18]([CH3:20])([CH3:17])[O:16][CH2:5]2)[CH2:14][O:3]1

Participants

5

Reactant 2

HCID 6251MannitolHCID 88306345HCID 88306345, compound

Product 1

HCID 960111,2:5,6-Di-O-isopropylidene-D-mannitol

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 180AcetoneSolvent

Procedure

In the preparation of the diketonide deriving from D-mannitol acetone is the ketone which is preferentially used. Then, the 1,2,5,6-diacetone D-mannitol is prepared by reacting acetone, to which solid zinc chloride has been added, with D-mannitol with stirring within a temperature range of from 0° C. to +50° C.

Workup

  1. customIn the preparation of the diketonide

Sources & evidence

ORD record
ord-d50c5cfb9ad14af39c5720aa3c0be4ce
Source dataset
uspto-grants-1983_11
Patent number
US04413142

Reaction notes

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