Toluene → Nonane

HRID 2226413Notes

Reaction equation

HRID 2226413 reaction equation
CO[CH:3](OC)[CH2:4][CH2:5][C:6]1(N)[CH2:10][CH2:9][CH2:8][CH2:7]1.[C:14]1(C)C=CC=CC=1>[Ni].CC(C)=O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:14][CH2:7][CH2:8][CH2:9][CH2:10][CH2:6][CH2:5][CH2:4][CH3:3]

Participants

6

Reactant 2

HCID 1140TolueneHCID 19920138HCID 19920138, compound

Product 1

HCID 8141Nonane

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 180AcetoneSolventHCID 6101p-Toluenesulfonic acidSolvent

Procedure

Condense nitrocyclopentane (prepared from bromocyclopentane and sodium nitrite) and acrolein in tetrahydrofuran in the presence of sodium hydride to obtain 3-(1-nitrocyclopentyl)propionaldehyde. Treat this aldehyde with p-toluenesulfonic acid in methanol and isolate 3-(1-nitrocylopentyl) propionaldehyde dimethyl acetal. Hydrogenate this compound with Raney nickel. Isolate 3-(1-aminocyclopentyl)propionaldehyde dimethylacetal and dissolve in aqueous acetone in the presence of p-toluenesulfonic acid and heat under reflux, followed by addition of toluene and azeotrope the mixture to give 1-azaspiro[4.4]-Δ1 -nonane.

Workup

  1. temperatureheat
  2. temperatureunder reflux

Sources & evidence

ORD record
ord-192e3b8974e140a4809ec826b27fa68c
Source dataset
uspto-grants-1994_09
Patent number
US05348944

Reaction notes

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