By Alexander R. Surrey (Auth.)
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1 RMgX + R'R"NCHO » RCHO + R'R"NH + MgX T h e main side reaction in this synthesis is the formation of tertiary amines according to the following equation: 2 2RMgX + HCONR'R" *> R CHNR'R" + MgO + MgX, Smith and co-workers ' have investigated the use of Grignard reagents in t h e preparation of aldehydes. Using t h e Bouveault synthesis, they obtained a 50% yield of o-tolualdehyde from o-bromotoluene and N-methylformanilide. 2 2 3 1 CH CH O Br MgBr 3 HCON-C H 6 5 r^jiCHO CH * kJtQlh In a similar m a n n e r t h e meta a n d para isomers were p r e p a r e d in 33% a n d 37% yield, respectively.
Wiley, New York, 1944. 2 . L. Claisen, Ber. deut. Chem. Ges. 45, 3157 (1912). 3. L. Claisen and E. Tietze, Ber. deut. Chem. Ges. 58, 275 (1925). 4. H. Schmid and K. Schmid, Helv. Chim. Acta 35, 1879 (1952). 5. E. R. Alexander and R. W. Kluiber, /. Am. Chem. Soc. 73, 4304 (1951). 6. M. S. Kharasch, G. Stampa, and W. Nudenberg, Science 1 1 6 , 309 (1952). 7. W. Gerrard, M. F. Lappert, and H. B. Silver, Proc. Chem. Soc. p. 19 (1957). 8. See D . Y. Curtin and H. W. Johnson, /. Am. Chem. Soc. 78, 2611 (1956).
Chem. Soc. 79, 3156 (1957). 51 Claisen-Schmidt Condensation Another reaction associated with Claisen is t h e Claisen-Schmidt condensation. -unsaturated a l d e h y d e or ketone. Benzylideneacetophen o n e m a y b e p r e p a r e d b y this m e t h o d in 85% yield from b e n z a l d e h y d e and acetophenone. 1 -H20 C H CHO + CH COC H 6 6 3 6 • 5 CeEUCH^CHCOCeHs This p r o d u c t is also k n o w n u n d e r t h e n a m e chalcone. Its derivatives h a v e b e e n the subject of w i d e investigation in connection with antibacterial activity.
