tert-Butyl hydroperoxide → HCID 19013691, compound

HRID 1729113Notes

Reaction equation

HRID 1729113 reaction equation
[F:1][C:2]([F:22])([C:6]([F:21])([F:20])[C:7]([F:19])([F:18])[C:8]([F:17])([F:16])[C:9]([F:15])([F:14])[C:10]([F:13])([F:12])[F:11])[CH2:3][CH:4]=[CH2:5].[CH:23]1[CH2:27][CH:26]=[CH:25][CH:24]=1.C([O:32]O)(C)(C)C>C1(C)C=CC=CC=1>[O:32]1[CH:23]2[CH:24]1[CH:25]1[CH2:26][CH:27]2[CH:4]([CH2:3][C:2]([F:22])([F:1])[C:6]([F:20])([F:21])[C:7]([F:18])([F:19])[C:8]([F:16])([F:17])[C:9]([F:14])([F:15])[C:10]([F:13])([F:12])[F:11])[CH2:5]1

Participants

5

Reactant 3

HCID 6410tert-Butyl hydroperoxideHCID 7612CyclopentadieneHCID 111004734,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-1-nonene

Product 1

HCID 19013691HCID 19013691, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

10.7 g (25 mmol) of the Diels-Alder product of 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-1-nonene (perfluorohexyl-1-propene) and cyclopentadiene are mixed in 10 ml of dry toluene with 326 mg (1 mmol) of molybdenum acetylacetonate, and 13 ml of a2.9 molar solution of t-butyl hydroperoxide in toluene (37.5 mmol) are added dropwise at 22° C. within 30 minutes. During this period, thetemperature rises to 60° C. The solution is then held at 60° C. for another 2 hours. The low-boiling components are distilled off underreduced pressure at 40° C., and the residue is chromatographed on silica gel. The mobile solvent used is a mixture of hexane/methylene chloride/diethyl ether (10:10:0.5 parts by volume). The product-containingfractions are combined. After the mobile solvent is distilled off, 7.3 g ofa white solid remain behind.

Workup

  1. additionare added dropwise at 22° C. within 30 minutes
  2. waitDuring this period
  3. customrises to 60° C
  4. distillationThe low-boiling components are distilled off underreduced pressure at 40° C.
  5. customthe residue is chromatographed on silica gel
  6. additiona mixture of hexane/methylene chloride/diethyl ether (10:10:0.5 parts by volume)
  7. distillationAfter the mobile solvent is distilled off

Sources & evidence

ORD record
ord-77a80e8914bc42ee925b3bdbd4408674
Source dataset
uspto-grants-1994_07
Patent number
US05331084

Reaction notes

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