Sodium Iodide → 1,2-Octanediol

HRID 1648832Notes

Reaction equation

HRID 1648832 reaction equation
[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5]CCC.[Na+].[I-].[C:11]([O:15]O)(C)([CH3:13])[CH3:12].[O-:17]O>C(O)(C)(C)C.O>[CH2:12]([OH:17])[CH:11]([OH:15])[CH2:13][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 6410tert-Butyl hydroperoxideHCID 81251-OcteneHCID 18500Perhydroxyl radical

Product 1

HCID 142311,2-Octanediol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent2×

Procedure

Into a 100 ml 3-neck flask provided with condenser, addition funnel, and magnetic stirrer is charged t-butyl-alcohol (20.0 g), 1-octene (4.48 g), water (1.0 g), NaI (0.03 g) and 0.30 g of the Os(CO)12 /MgO supported catalyst prepared in accordance with Example 1. At ambient temperature (26° C.), 2.0 g of a solution of 90% by weight, tertiary butyl hydroperoxide dissolved in t-butyl alcohol is added dropwise over a period of 2 minutes with stirring. After 12 hours from completion of the addition, the reaction mixture is analyzed by GLC and complete conversion of the hydroperoxide is obtained with a selectivity to 1,2-octanediol of 84%. The results are summarized at Table 1.

Workup

  1. customInto a 100 ml 3-neck flask provided with condenser, addition funnel, and magnetic stirrer
  2. customprepared in accordance with Example 1
  3. additionis added dropwise over a period of 2 minutes
  4. additionAfter 12 hours from completion of the addition

Sources & evidence

ORD record
ord-4827ab09b1c74073ab269da1b37c4b92
Source dataset
uspto-grants-1983_11
Patent number
US04413151

Reaction notes

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