Mannitol → HCID 21918198, compound

HRID 266012Notes

Reaction equation

HRID 266012 reaction equation
C(O)[C@H:2]([C@H:4]([C@@H:6]([C@@H:8]([CH2:10][OH:11])[OH:9])[OH:7])O)O.[C:13]([O-])(O)=O.[Na+].I([O-])(=O)(=O)=O.[Na+]>C(Cl)Cl>[C:4](=[C:6]([OH:7])[CH:8]([OH:9])[CH:10]=[O:11])([CH3:2])[CH3:13]

Participants

5

Reactant 3

HCID 6251MannitolHCID 516892Sodium BicarbonateHCID 23667635Sodium periodate

Product 1

HCID 21918198HCID 21918198, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The mannitol derivative of Example 7(a) (81 g, 0.311 mol) was suspended in CH2Cl2 (1.1 L) and saturated NaHCO3 (40 mL) and stirred at ambient temperature. Sodium periodate (100 g, 0.47 mol) was added in four portions over 20 minutes and the solution was stirred vigorously at 0° C. for 3 hours. The solvent was decanted off and the remaining solid was stirred in CH2Cl2 and then filtered to remove the excess solid. The two organic portions were combined and concentrated in vacuo. The resulting oil was distilled at reduced pressure to give the title product as a clear, viscous oil. Yield (59 g, 75%). 1H NMR (CDCl3) δ 4.3 (t, 1 H), 3.9 (m, 2 H), 1.4 (d, 6 H).

Workup

  1. customThe solvent was decanted off
  2. stirringthe remaining solid was stirred in CH2Cl2
  3. filtrationfiltered
  4. customto remove the excess solid
  5. concentrationconcentrated in vacuo
  6. distillationThe resulting oil was distilled at reduced pressure

Sources & evidence

ORD record
ord-5bb873955fb7461d9a02633062fd4579
Source dataset
uspto-grants-1997_07
Patent number
US05650133

Reaction notes

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