HCID 66743944, compound → HCID 69087138, compound

HRID 1923450Notes

Reaction equation

HRID 1923450 reaction equation
[CH3:1][C:2]12[O:11][C:10]([CH3:12])=[CH:9][CH:8]3[CH2:13][CH:14]([CH3:15])[CH:5]([CH2:6][CH:7]13)[CH2:4][CH2:3]2.[H][H]>[Pd].CC(O)C>[CH3:1][C:2]12[O:11][CH:10]([CH3:12])[CH2:9][CH:8]3[CH2:13][CH:14]([CH3:15])[CH:5]([CH2:6][CH:7]13)[CH2:4][CH2:3]2

Participants

5

Reactant 2

HCID 66743944HCID 66743944, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69087138HCID 69087138, compoundYield 92.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

In an autoclave, 4,6,11-trimethyl-5-oxa-tricyclo[6.2.2.0*4,9*]dodec-6-ene (770 g, obtained as above) and palladium (5%, 7.6 g) on carbon was added to 2-propanol (100 g). The reaction mixture was stirred at a temperature between 70-100° C. under a pressure of 300 psi hydrogen for 6 hours. GC analysis indicated that the reaction was completed. The resulting material was then filtered and distilled under a reduced pressure to provide 4,6,11-trimethyl-5-oxa-tricyclo[6.2.2.0*4,9*]dodecane (720 g), which had a boiling point of 132° C. at a pressure of 0.8 mmHg

Workup

  1. filtrationThe resulting material was then filtered
  2. distillationdistilled under a reduced pressure

Sources & evidence

ORD record
ord-d6d5bedd392947d4aecd30bb38dd1dab
Source dataset
uspto-grants-2012_05
Patent number
US08178485B2

Reaction notes

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