Oxygen → HCID 54574644, compound

HRID 1414836Notes

Reaction equation

HRID 1414836 reaction equation
[CH2:1]([Mg]Br)[CH:2]=[CH2:3].[CH:6]12[CH2:12][CH:9]([CH:10]=[CH:11]1)[CH:8]=[CH:7]2.[O:13]=O.[Cl-].[NH4+]>C(OCC)C.O>[CH:2]12[CH2:1][CH:9]([CH:10]=[CH:11]1)[CH:8]1[CH:3]2[CH:6]([CH2:12][OH:13])[CH2:7]1

Participants

7

Reactant 4

HCID 977OxygenHCID 8473NorbornadieneHCID 25517Ammonium ChlorideHCID 178455850HCID 178455850, compound

Product 1

HCID 54574644HCID 54574644, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Conditions

Temperature
140 °C

Procedure

Allylmagnesium bromide (50 mmoles) and bicyclo[2.2.1]hepta-2,5-diene (50 mmoles) were reacted in diethyl ether in a sealed bomb by heating for 2.25 hours at 125° C. and one hour at 140° C. The reaction product was then oxidized at 0° C. by passing gaseous oxygen through the product for about 30 minutes. The resultant product was then hydrolyzed with water followed by aqueous ammonium chloride solution and then water. After drying the product over anhydrous magnesium sulfate, the diethyl ether solvent was removed using a steam bath. The product was vacuum distilled and the fraction boiling at 95°-101° C. at 2.5-3 mm Hg was collected. This product, tricyclo[4.2.1.02,5 ]non-7-en-3-ylmethanol, was isolated in a 70 percent yield and its structure was supported by the results of nuclear magnetic resonance studies. It may be depicted as follows: ##STR1##

Workup

  1. customwas then oxidized at 0° C.
  2. customfor about 30 minutes
  3. dry with materialAfter drying the product over anhydrous magnesium sulfate
  4. customthe diethyl ether solvent was removed
  5. distillationdistilled
  6. customthe fraction boiling at 95°-101° C. at 2.5-3 mm Hg was collected

Sources & evidence

ORD record
ord-3525363c882d4be88a2590a54b50313a
Source dataset
uspto-grants-1977_01
Patent number
US04002691

Reaction notes

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