Methanol → 4-(m-Phenoxyphenyl)-2-pentanone

HRID 1074569Notes

Reaction equation

[O:1]([C:8]1[CH:9]=[C:10]([CH:14]([CH3:19])[CH2:15][C:16](Cl)=[O:17])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20](Cl)(=O)C(Cl)=O.[Li].C[Cu]C.CO>C1C=CC=CC=1.CCOCC.O>[O:1]([C:8]1[CH:9]=[C:10]([CH:14]([CH3:19])[CH2:15][C:16](=[O:17])[CH3:20])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -70 °C

Procedure

A solution of 3-(m-phenoxyphenyl)-butyryl chloride (1 g.) (from the corresponding acid (1 g.) using excess oxalyl chloride in benzene) in ether (20 ml) was added dropwise to a solution of dimethyl copper lithium at -70° C. under nitrogen (from methyl lithium (0.2 g.) and cuprous iodide (1 g.)) in ether (50 ml) and the mixture stirred a further 15 minutes at -70° C. Methanol was added to quench the reaction and the mixture was diluted with water, acidified and filtered through a pad of Kieselguhr. The ether layer was washed with sodium carbonate solution and with water, dried over anhydrous magnesium sulphate and evaporated to give a colourless oil. The product was purified by column chromatography to give 4-(m-phenoxyphenyl)-2-pentanone as a colourless oil.

Workup

customto quench
customthe reaction
filtrationfiltered through a pad of Kieselguhr
washThe ether layer was washed with sodium carbonate solution and with water
dry with materialdried over anhydrous magnesium sulphate
customevaporated
customto give a colourless oil
customThe product was purified by column chromatography

Sources & evidence

ORD record: ord-76d3849e2ac94b6c9a0e2a101968f6c5
Source dataset: uspto-grants-1983_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04393079

Reaction notes

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