Formic Acid → 2,3-Dihydroxy-5-(perfluorohexyl)bicyclo[2.2.1]heptane

HRID 486981Notes

Reaction equation

HRID 486981 reaction equation
[F:1][C:2]([F:21])([C:5]([F:20])([F:19])[C:6]([F:18])([F:17])[C:7]([F:16])([F:15])[C:8]([F:14])([F:13])[C:9]([F:12])([F:11])[F:10])[CH:3]=[CH2:4].[CH:22]1C[CH:25]=[CH:24][CH:23]=1.[OH:27]O.[CH:29]([OH:31])=O>>[OH:27][CH:22]1[CH:29]([OH:31])[CH:25]2[CH2:24][CH:23]1[CH2:4][CH:3]2[C:2]([F:21])([F:1])[C:5]([F:19])([F:20])[C:6]([F:17])([F:18])[C:7]([F:15])([F:16])[C:8]([F:13])([F:14])[C:9]([F:12])([F:11])[F:10]

Participants

5

Reactant 4

HCID 284Formic AcidHCID 784Hydrogen PeroxideHCID 7612CyclopentadieneHCID 91384(Perfluorohexyl)ethylene

Product 1

HCID 190970052,3-Dihydroxy-5-(perfluorohexyl)bicyclo[2.2.1]heptane

Procedure

8.2 g (20 mmol) of the Diels-Alder reaction product of 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-1-octene (perfluorohexylethene) and cyclopentadiene are mixed with 20 ml of formic acid, 1.3 ml of 70 percent strength hydrogen peroxide (30 mmol) is added at 60° C., and the mixture is held at 60° C. for 36 hours. The low-boiling components are distilled off in vacuo. The residue is extracted with three portions (130 ml in total) of methylene chloride. The combined extracts are dried with magnesium sulfate and the methylene chloride is removed in vacuo. The residue is sublimed at 95° C. in an oil pump vacuum.

Workup

  1. additionis added at 60° C.
  2. distillationThe low-boiling components are distilled off in vacuo
  3. extractionThe residue is extracted with three portions (130 ml in total) of methylene chloride
  4. dry with materialThe combined extracts are dried with magnesium sulfate
  5. customthe methylene chloride is removed in vacuo
  6. customis sublimed at 95° C. in an oil pump vacuum

Sources & evidence

ORD record
ord-d181e0f70cb34459820915525b70489f
Source dataset
uspto-grants-1994_03
Patent number
US05292971

Reaction notes

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