Methane → HCID 13406938, compound

HRID 2286464Notes

Reaction equation

HRID 2286464 reaction equation
[CH:1]([CH:3]1[CH:8]([C:9]([O:11][CH3:12])=[O:10])[CH:7]2[CH2:13][CH:4]1[CH:5]=[CH:6]2)=[O:2].C>C(OCC)(=O)C.[Pd]>[CH:1]([CH:3]1[CH:8]([C:9]([O:11][CH3:12])=[O:10])[CH:7]2[CH2:13][CH:4]1[CH2:5][CH2:6]2)=[O:2]

Participants

5

Reactant 2

HCID 297MethaneHCID 23463503HCID 23463503, compound

Product 1

HCID 13406938HCID 13406938, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4 g (0.022 mole) of methyl 2-formyl-bicyclo[2.2.1]hept-5-en-3-yl-carboxylate--see Example 2 above--in 60 ml of ethyl acetate were hydrogenated in the presence of 100 mg of 10% Pd over charcoal at atmospheric pressure and at room temperature. After absorption (about 1 h) of the theoretical quantity of hydrogen, the reaction mixture was filtered and the clear filtrate was concentrated under reduced pressure. The obtained residue was distilled (pressure: 0.06 Torr/bath temperature: 82°-115°) to yield 3.27 g (yield 82%) of the title compound.

Workup

  1. customAfter absorption (about 1 h) of the theoretical quantity of hydrogen
  2. filtrationthe reaction mixture was filtered
  3. concentrationthe clear filtrate was concentrated under reduced pressure
  4. distillationThe obtained residue was distilled (pressure: 0.06 Torr/bath temperature: 82°-115°)

Sources & evidence

ORD record
ord-dbcd5dff7dc2441390f0ea37b0523e88
Source dataset
uspto-grants-1981_05
Patent number
US04266075

Reaction notes

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