Water → 145486-31-3

HRID 1033431Notes

Reaction equation

HRID 1033431 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, 200 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-86bbd5393f244782978e3326ac084cc1
Source dataset
uspto-grants-1994_05
Patent number
US05310737

Reaction notes

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