Water → 145486-31-3

HRID 1591488Notes

Reaction equation

HRID 1591488 reaction equation
O.[CH2:2]([O:9][C:10]([CH3:14])([CH:12]=C)[CH3:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.I([O-])(=O)(=O)=[O:16].[Na+]>[Os](=O)(=O)(=O)=O.O1CCOCC1>[CH2:2]([O:9][C:10]([CH3:11])([CH3:14])[CH:12]=[O:16])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 962WaterHCID 10487510HCID 10487510, compoundHCID 23667635Sodium periodate

Product 1

HCID 10986836145486-31-3Yield 37%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 100 mL of water, 300 mL of dioxane, 20 g (0.11 mol) of 2-benzyloxy-2-methyl-3-butene and 1 g of osmium tetroxide was stirred at room temperature for 30 minutes then 51 g (0.22 mol) of finely ground sodium periodate was added in portions over 30 minutes. Stirring was continued for 2 hours then the mixture filtered and the filtrate extracted with several portions of ether. The combined extracts were dried over magnesium sulfate, filtered and the filtrate concentrated under vacuum. Distillation afforded 7.3 g (0.041 mol,37%) of product, b.p. 85°-88° C. (2 mm).

Workup

  1. stirringStirring
  2. waitwas continued for 2 hours
  3. filtrationthe mixture filtered
  4. extractionthe filtrate extracted with several portions of ether
  5. dry with materialThe combined extracts were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under vacuum
  8. distillationDistillation

Sources & evidence

ORD record
ord-aad0df56932641faa355f007c32be21b
Source dataset
uspto-grants-1993_04
Patent number
US05206235

Reaction notes

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