Ammonia → Cyclohexanone, 4,4-dimethyl-2-(2-propenyl)-

HRID 863178Notes

Reaction equation

[CH3:1][C:2]1([CH3:9])[CH2:7][CH2:6][C:5](=[O:8])[CH:4]=[CH:3]1.[Li].N.[CH2:12](Br)[CH:13]=[CH2:14]>O1CCCC1.C(OCC)(=O)C>[CH3:1][C:2]1([CH3:9])[CH2:7][CH2:6][C:5](=[O:8])[CH:4]([CH2:14][CH:13]=[CH2:12])[CH2:3]1

Participants

Conditions

Temperature: -33 °C

Procedure

A solution of 4,4-dimethyl-2-cyclohexen-1-one (500 mg) in dry tetrahydrofuran (2 ml) was added to a well stirred solution of lithium (141 mg) in liquid ammonia (5 ml), The mixture was stirred at -33° C. for 1 hr. And then, to this solution allyl bromide (2.4 g) was added, and stirred for 30 min. The reaction was quenched by addition of methanol, and the ammonia was allowed to evaporate. The residue was diluted with water, and extracted with diethyl ether. The organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated. Purification of the residue with silica gel column chromatography (using n-hexane:ethyl acetate=30:1 as an eluent) gave 4,4-dimethyl-2-(2-propenyl)cyclohexanone (345 mg, 52% yield) as a colorless oil.

Workup

stirringstirred for 30 min
customThe reaction was quenched by addition of methanol
customto evaporate
additionThe residue was diluted with water
extractionextracted with diethyl ether
washThe organic extracts were washed with brine
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated
customPurification of the residue with silica gel column chromatography (

Sources & evidence

ORD record: ord-8d9dfe81d32b49a3ad88dc6669b361e7
Source dataset: uspto-grants-1998_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05719291

Reaction notes

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