tert-Butyl hydroperoxide → HCID 20222582, compound

HRID 979754Notes

Reaction equation

HRID 979754 reaction equation
[CH3:1][C:2]1([CH3:14])[C:11]2[CH2:10][CH:9]=[CH:8][CH2:7][C:6]=2[C:5]([CH3:13])([CH3:12])[CH2:4][CH2:3]1.P([O-])([O-])(O)=[O:16].[Na+].[Na+].C(OO)(C)(C)C>ClCCCl.[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo]>[O:16]1[CH:8]2[CH:9]1[CH2:10][C:11]1[C:2]([CH3:14])([CH3:1])[CH2:3][CH2:4][C:5]([CH3:13])([CH3:12])[C:6]=1[CH2:7]2

Participants

6

Reactant 3

HCID 6410tert-Butyl hydroperoxideHCID 24203Sodium Phosphate, DibasicHCID 20222602HCID 20222602, compound

Product 1

HCID 20222582HCID 20222582, compound

Reagents, catalysts & solvents 2

HCID 98885Molybdenum carbonyl (Mo(CO)6)CatalystHCID 111,2-DichloroethaneSolvent

Procedure

35 g of a hydrocarbon mixture containing (according to GC) 43% of 1,1,4,4-tetramethyl-1,2,3,4,5,8-hexahydronaphthalene (IIh) are dissolved in 140 ml of 1,2-dichloroethane and treated in accordance with method C described in Example 1 with 0.304 g of molybdenum hexacarbonyl, 0.1148 g of disodium hydrogen phosphate and 65 ml of 2.85 molar tert.butyl hydroperoxide solution. After working-up, 30 g of crude product are obtained. 10 g thereof are chromatographed on 600 g of silica gel Merck (0.04-0.063 mm) (elution agent: 2-3% ether/hexane). 1.9 g of 6,7-epoxy-1,1,4,4-tetramethyl-1,2,3,4,5,6,7,8-octahydro-naphthalene are obtained.

Workup

  1. additiontreated in accordance with method C
  2. custom30 g of crude product are obtained
  3. custom10 g thereof are chromatographed on 600 g of silica gel Merck (0.04-0.063 mm) (elution agent: 2-3% ether/hexane)

Sources & evidence

ORD record
ord-aa8dea30ed08411cb111bd81bde696c9
Source dataset
uspto-grants-1987_01
Patent number
US04634548

Reaction notes

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