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8561616 
Journal Article 
Selective Ortho Alkylation of Phenols in the Presence of Metallic Sodium 
Yamada, S; Ono, F; Katagiri, T; Tanaka, J 
1980 
1 
Nippon Kagaku Kaishi
ISSN: 0369-4577
EISSN: 2185-0925 
CHEMICAL SOC JAPAN 
TOKYO 
1980 
5 
733-737 
English 
WOS:A1980JT09800011 
The reaction of phenol with l-chloro-3-methyl-2-butene (prenyl chloride) in the presence of alkali metal was found to be completed in only 30 minutes at relatively low temperature (30 ∼40°C). Other alkyl halides, such as cinnamyl chloride, benzyl chloride, trans-l-chloro-2-butene arid trams-l-chloro-2-hexene, reacted with phenol under the same conditions, and the corresponding o-alkylated phenols were obtained in the yields of 71, 87, 88 and 84%, respectively. In the case of saturated alkyl halides, such, as ethyl chloride, butyl chloride, pentyl chloride and isopentyi chloride, however, the corresponding products could not be obtained. The selectivity for o-substituted phenols was found to be governed by solvent, reaction time, reaction temperature and water present in a solvent. On the basis of these results, the reaction scheme is discussed. © 1980, The Chemical Society of Japan. All rights reserved.