HCID 66584180, compound → HCID 66584264, compound

HRID 716501Notes

Reaction equation

HRID 716501 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH:7]([CH3:14])[CH2:8][C:9]1[CH2:13][CH2:12][CH2:11][CH:10]=1)(=[O:3])[CH3:2].[H][H]>[Ni].[Pd].C(O)(C)C>[C:1]([O:4][CH2:5][CH2:6][CH:7]([CH3:14])[CH2:8][CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13]1)(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 66584180HCID 66584180, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66584264HCID 66584264, compoundYield 93%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

A solution of 4-cyclopentenyl-3-methylbutyl acetate (1.96 kg, 10.0 mols), isopropyl alcohol (1000 ml) and Raney nickel (100 g), Pd/C 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-cyclopentyl-3-methylbutyl acetate (1.84 kg, yield: 93%, purity: 98%.

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-84305eab671843ffa63da750c105ddd3
Source dataset
uspto-grants-2015_11
Patent number
US09187709B2

Reaction notes

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