3-Heptylidene-5-methyloxolan-2-one → 2(3H)-Furanone, 3-heptyldihydro-5-methyl-

HRID 1111314Notes

Reaction equation

HRID 1111314 reaction equation
[CH:1](=[C:8]1[CH2:12][CH:11]([CH3:13])[O:10][C:9]1=[O:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]>[Pd].C(O)C>[CH2:1]([CH:8]1[CH2:12][CH:11]([CH3:13])[O:10][C:9]1=[O:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

4

Reactant 1

HCID 543179383-Heptylidene-5-methyloxolan-2-one

Product 1

HCID 619902(3H)-Furanone, 3-heptyldihydro-5-methyl-Yield 98.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Using the same general hydrogenation procedure described in Example I, 3-heptylidene-5-methyldihydro-2(3H)-furanone (10 g; 0.051 mole) was combined with 0.5 g 5% palladium on carbon catalyst and 10 ml ethanol. Hydrogen gas was bubbled into the mixture over a 12 hour period with stirring. After removal of the catalyst and evaporation of the solvent, 9.95 g (96% assay by GLC; 95% yield) 3-heptyl-5-methyldihydro-2(3H)-furanone was recovered. The proton nuclear resonance spectrum for the product was as follows:

Workup

  1. customHydrogen gas was bubbled into the mixture over a 12 hour period

Sources & evidence

ORD record
ord-046f0365d5fc476481edb8c8a1b0866d
Source dataset
uspto-grants-1990_12
Patent number
US04980342

Reaction notes

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