Organic Syntheses, CV 7, 361
Submitted by S. A. Buntin and R. F. Heck
1.
Checked by C. M. Tice and C. H. Heathcock.
1. Procedure
A
250-mL, three-necked, round-bottomed flask, equipped with a mechanical stirrer and a
reflux condenser, is charged with
0.49 g (2.2 mmol) of palladium acetate (Note
1),
20.4 g (100 mmol) of iodobenzene,
9.0 g (125 mmol) of 2-methyl-2-propen-1-ol,
12.6 g (125 mmol) of triethylamine, and
32.5 mL of acetonitrile (Note
2). The reaction vessel is placed in an
oil bath at 100°C and the solution is heated to reflux for 11 hr under a
nitrogen atmosphere. The reaction mixture is allowed to cool to room temperature and transferred to a
500-mL separatory funnel with the aid of
100 mL of ether and 100 mL of water. The organic layer is washed five times with 100 mL portions of water. The combined aqueous layers are reextracted with
100 mL of ether. The organic layers are combined, dried over anhydrous
sodium carbonate, and filtered. The organic layer is concentrated and distilled under reduced pressure. The product,
2-methyl-3-phenyl-propanal, 12.05 g (82%), has a boiling range of
52–58°C at 0.40 mm (Note
3).
2. Notes
1.
Palladium acetate was prepared by the method of Stephenson et al.
2 A suitable material is also available from the Strem Chemical Company or Alfa Inorganics.
3. Discussion
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