HCID 543425, compound → HCID 53818969, compound

HRID 583639Notes

Reaction equation

HRID 583639 reaction equation
[CH:1]([C:3]1(O)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)=[CH2:2]>C[Re](=O)(=O)=O.C1(C)C=CC=CC=1>[CH:1]([C:3]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH:4]=1)=[CH2:2]

Participants

4

Reactant 1

HCID 543425HCID 543425, compound

Product 1

HCID 53818969HCID 53818969, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 178477782HCID 178477782, compoundCatalystHCID 1140TolueneSolvent

Procedure

A solution of 1.20 grams of 1-vinylcyclododecanol, 10 ml of toluene, and 20 mg of methylrhenium trioxide was refluxed 4 hrs, by which time VPC and TLC analyses indicated complete consumption of the starting material. The mixture was cooled, washed with 5% aqueous sodium carbonate solution to remove catalyst, and the organic phase dried (magnesium sulfate) and stripped of volatiles at reduced pressure. There was obtained 1.02 gram (93%) of 1-vinylcyclododecene as ca. 2:1 trans:cis mixture (VPC); NMR spectrum was in good agreement with that expected for the product.

Workup

  1. customconsumption of the starting material
  2. temperatureThe mixture was cooled
  3. washwashed with 5% aqueous sodium carbonate solution
  4. customto remove catalyst
  5. dry with materialthe organic phase dried (magnesium sulfate)

Sources & evidence

ORD record
ord-00e3498241ba40af84553ef540f4baba
Source dataset
uspto-grants-1999_07
Patent number
US05929298

Reaction notes

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