Cl[C:2]1[CH:7]=[CH:6][C:5](CC#C)=[CH:4][CH:3]=1.[CH2:11]([Li])[CH2:12][CH2:13]C.[CH2:16]=[O:17].[Cl-:18].[Na+]>CCOCC.CCCCCC>[Cl:18][C:2]1[CH:7]=[CH:6][C:5]([CH:16]([OH:17])[C:11]#[C:12][CH3:13])=[CH:4][CH:3]=1Under nitrogen and with cooling, to a solution of 150.6 g (1.0 mole) 1-chloro-4-(2-propynyl)benzene in 600 ml of anhydrous ether, add dropwise 400 ml of 2.5M n-butyllithium (1.0 mole) in hexane. When addition is complete, stir a further 30 minutes and under N2 add 31 g of para-formaldehyde. Stir the mixture in a dry ice/acetone bath for 1 hour. Allow to warm to room temperature and then allow to reflux. When the reaction is complete, add 400 ml of saturated aqueous sodium chloride. Separate the layers and extract the aqueous layer with ether. Wash the combined ether solution, wash with water and dry over magnesium sulfate. Evaporate off the ether, dissolve the residue in hot cyclohexane which yielded crystalline material the title compound.
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