Semi-Sintesis Vanili dari Guaiakol Via Reaksi Reimer-Tiemann yang dikatalisis dengan Katalis Transfer Fase/Ptc: [18]-Crown Ether-6

Abstract

Reimer-Tiemann reaction belongs to the group of the electrophylic substitution reaction (SE), and principally, this reaction consists of three steps reactions, namely: 1. formation of dichlorocarbene from chloroform by action of base (i.e. KOH), 2. reaction of dichlorocarbene as electrophyl to the benzene (or general aromatic) nucleus, 3. hydrolysis of the formed dichloromethyl benzene to the derivative of benzaldehyde. In this work has been carried out the modification of Reimer-Tiemann reaction with the goal to synthesize vanillin from guaiacol (o-methoxyphenol) as well as to compare with the conventional Reimer-Tiemann reaction. By the way, the modification of Reimer-Tiemann by using phase transfer catalyst and ethanol as co-solvent can obviously enhance the yield of vanillin up to 51.2% compared with the yield of conventional Reimer-Tiemann to synthesize of vanillin (up to 24.4%).

Keywords

• Reimer-Tiemann reaction
• guaiacol
• chloroform
• vanillin