Methyl vinyl ketone → [7-(1-Ethyl-propylidene)-bicyclo[2.2.1]hept-2-yl]ethanone

HRID 1828672Notes

Reaction equation

[CH2:1]([C:3]([CH2:9][CH3:10])=[C:4]1[CH:8]=[CH:7][CH:6]=[CH:5]1)[CH3:2].[CH3:11][C:12](C=C)=[O:13].[C:16]1(C)C=CC=C[CH:17]=1.CCCCCC>[Pd]>[CH2:1]([C:3](=[C:4]1[CH:8]2[CH2:16][CH2:17][CH:5]1[CH:6]([C:12](=[O:13])[CH3:11])[CH2:7]2)[CH2:9][CH3:10])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 6,6-diethyl-fulvene (prepared as described in J. Org. Chem., 1990, 55, 3395; 86.0 g, 0.64 mol) and methyl-vinyl-ketone (44.9 g, 0.64 mol) was stirred for 5 h at 50° C. The mixture was cooled to room temperature and diluted with toluene/hexane (1/9, 600 ml). The solution was hydrogenated at normal pressure using palladium on charcoal (10%) as a catalyst. After 5 h the mixture was filtered, concentrated in vacuo and the residue was distilled (bp. 70° C./0.01 Torr) to yield the title compound (65.5 g, 50%) as a mixture of 2 isomers in a ratio of 3:1. Odor description: Woody, floral, Vertofix, Lilial, ambery.

Workup

temperatureThe mixture was cooled to room temperature
filtrationAfter 5 h the mixture was filtered
concentrationconcentrated in vacuo
distillationthe residue was distilled (bp. 70° C./0.01 Torr)

Sources & evidence

ORD record: ord-624af58861444747ba054c44d5aff94f
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07060664B2

Reaction notes

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