[CH3:1][C:2]([CH3:6])([CH3:5])[C:3]#N.[Cl:7][C:8]1[CH:13]=[CH:12][C:11](I)=[CH:10][CH:9]=1.[Mg].[OH:16]S(O)(=O)=O>O1CCCC1.[Na].O>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:3]([C:2]([CH3:6])([CH3:5])[CH3:1])=[O:16])=[CH:10][CH:9]=1
Trimethyl acetonitrile (0.1 mol) in dry tetrahydrofuran (50 ml) was added dropwise with stirring to the Grignard reagent prepared form 4-chloro-iodobenzene (0.11 mol) and magnesium turnings (0.11 g atoms) in sodium dry ether (50 ml) at such a rate as to retain gentle reflux. The solution was refluxed for 4 hours, cooled to room temperature, and water (40 ml) added carefully. 2N H2SO4 (50 ml) was added and the ether solution washed with water (3×100 ml) and dried over anhydrous magnesium sulphate. Removal of the solvent gave a yellow oil which was distilled at the water pump to give tertiary butyl 4-chlorophenyl ketone (40%) as a colourless liquid b.p. 116°-128°/15 mm Hg.
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