tert-Butyl hydroperoxide → alpha-Hexyl-gamma-butyrolactone

HRID 894947

Reaction equation

HRID 894947 reaction equation
[C:1]([O-:4])(=[O:3])[CH3:2].[K+].[C:6](OO)(C)(C)[CH3:7].[CH3:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]C=C>C(O)(=O)C>[CH2:12]([CH:2]1[CH2:7][CH2:6][O:4][C:1]1=[O:3])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 6410tert-Butyl hydroperoxideHCID 81251-OcteneHCID 517044Potassium Acetate

Product 1

HCID 86736alpha-Hexyl-gamma-butyrolactoneYield 65%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
115 °C

Procedure

A stock solution was prepared by heating at 115° C. 500 milliliters of acetic acid, 150 grams of potassium acetate, and 245 grams of manganous acetate tetrahydrate, Mn(OCOCH3)2.4H2O. A 50-milliliter aliquot of the stock solution was added to 2 milliliters of a 0.312 molar solution of tertiary butyl hydroperoxide in acetic acid. The solution also contained 400 microliters of octene-1. After heating, a hexyl gamma-butyrolactone was obtained with a 65% yield based on the tertiary butyl hydroperoxide.

Workup

  1. customA stock solution was prepared
  2. temperatureAfter heating

Sources & evidence

ORD record
ord-b50eee57f5ae47179765aab26f16a942
Source dataset
uspto-grants-1981_08
Patent number
US04285868

Linked notes

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