[Mg].[Cl-].[CH3:3][CH2:4][CH2:5][C:6](=[O:11])[CH2:7][CH2:8][CH2:9][CH3:10].[CH2:12](Br)[C:13]#[CH:14].S(=O)(=O)(O)O>CCOCC.C1C=CC=CC=1>[OH:11][C:6]([CH2:12][CH2:13][CH3:14])([CH2:7][CH2:8][CH2:9][CH3:10])[CH2:5][C:4]#[CH:3]
14 Grams of powdered (50 mesh) magnesium metal is suspended in 80 ml of ether and activated by addition of 200 mg of mercurie chloride. A solution of 38.4 g of 4-octanone and 36.6 g of propargyl bromide in 120 ml of ether and 50 ml of benzene is added dropwise at a rate which produced a gentle reflux. After the addition is complete, the reaction mixture is stirred for several hours and is then poured into 500 ml of cold 5% sulfuric acid. The organic layer is separated, washed with water twice, dried over sodium sulfate and stripped of solvent. The residue is distilled under vacuum to give the title product.
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