1-Oxaspiro[5.5]undec-3-ene, 4-methyl- → HCID 3764775, compound

HRID 716484Notes

Reaction equation

HRID 716484 reaction equation
[CH3:1][C:2]1[CH2:7][C:6]2([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[O:5][CH2:4][CH:3]=1.[H][H]>[Ni].C(O)(C)C>[CH3:1][CH:2]1[CH2:7][C:6]2([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[O:5][CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 111164241-Oxaspiro[5.5]undec-3-ene, 4-methyl-HCID 178418361HCID 178418361, compound

Product 1

HCID 3764775HCID 3764775, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 3776IsopropanolSolvent

Procedure

A solution of 4-methyl-1-oxaspiro[5.5]undec-3-ene (1.66 kg, 10.0 mols), isopropyl alcohol (100 ml) and Raney nickel (100 g) or other suitable sponge-metal catalyst was hydrogenated at 400 psi, at 140° C. for 10-12 h until the theoretical amount of hydrogen was taken up. The mixture was cooled and filtrated. The isopropyl alcohol was evaporated and the residue obtained was distilled under reduced pressure to provide 4-methyl-1-oxaspiro [5.5] undecane (1.56 kg, yield: 93%, purity: 99% sum of the isomers).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltrated
  3. customThe isopropyl alcohol was evaporated
  4. customthe residue obtained
  5. distillationwas distilled under reduced pressure

Sources & evidence

ORD record
ord-3a6a16655d5743fc9ca3d68d22cd5821
Source dataset
uspto-grants-2015_11
Patent number
US09187709B2

Reaction notes

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