ChemInform Abstract: Unexpected Aldol Condensations under Williamson Arylmethyl Ether Synthesis Conditions.

✍ Scribed by A. L. SILVA; B. QUIROZ; L. A. MALDONADO

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 29 KB
• Volume: 29
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199825109

✦ Synopsis

Unexpected Aldol Condensations under Williamson Arylmethyl Ether Synthesis Conditions.

-O-Methylation of 5-bromosalicylaldehyde (Ia) under standard conditions using dimethyl sulfate in refluxing acetone for 2h gives the expected methyl ether (Va) in high yield. However, prolonged reflux leads to the unexpected formation of aldol product (IVa). The analogous phenolic aldehydes (Ib) and (Ic) undergo the same reaction to give the aldols (IVb) and (IVc). -(SILVA, A.