Isopropanol → HCID 21452015, compound

HRID 716496Notes

Reaction equation

HRID 716496 reaction equation
[CH3:1][C:2]1[CH2:7][C:6]2([CH2:12][CH:11]([CH3:13])[CH2:10][C:9]([CH3:15])([CH3:14])[CH2:8]2)CO[CH:3]=1.[H][H].[CH:18]([OH:21])(C)C>[Ni]>[CH3:1][CH:2]1[CH2:7][C:6]2([CH2:12][CH:11]([CH3:13])[CH2:10][C:9]([CH3:14])([CH3:15])[CH2:8]2)[O:21][CH2:18][CH2:3]1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 66584254HCID 66584254, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21452015HCID 21452015, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

A solution of 4,8,8,10-tetramethyl-2-oxaspiro [5.5] undec-3-ene (2.08 kg, 10.0 mols), isopropyl alcohol (1000 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 4,8,8,10-Tetramethyl-1-oxaspiro[5.5] undecane (1.89 kg, yield: 90%, purity: 97% 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-4883238c98bf4495bb2a42852e1c29f8
Source dataset
uspto-grants-2015_11
Patent number
US09187709B2

Reaction notes

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