Sodium Iodide → 1-[4-(Methoxymethyl)phenyl]propan-2-one

Reaction equation

C1[O:15][C:4]([CH3:14])([CH2:5][C:6]2[CH:11]=[CH:10][C:9]([CH2:12]Br)=[CH:8][CH:7]=2)OC1.[CH3:16][O-:17].[Na+].[I-].[Na+]>CO>[CH3:16][O:17][CH2:12][C:9]1[CH:8]=[CH:7][C:6]([CH2:5][C:4](=[O:15])[CH3:14])=[CH:11][CH:10]=1

Participants

Procedure

1-(4-Bromomethylphenyl)propan-2-one ethylene ketal (1.35 g) in methanol was added to sodium methoxide (from sodium (0.11 g)) in methanol containing a trace of sodium iodide. The mixture was refluxed for 1 hour. Methanol was removed, the residue partitioned between water and ether and the combined organic extracts dried. Removal of the solvent gave an oil which was dissolved in methanol-2 N hydrochloric acid and left for 1 hour at room temperature. Extraction with ether gave the title compound, bp 106°/0.7 mm. τ(CDCl3) 7.9 (3H, s), 7.63 (3H, s), 6.33 (2H, s), 5.54 (2H, s), 2.8 (2H, d, J=8 Hz), 2.6 (2H, d, J=8 Hz).