22571-39-7Relevant academic research and scientific papers
Synthesis of Two Naturally Occuring Oxygenated Oxiranes Related to Thymol
Sanghvi, Y. S.,Rao, A. S.
, p. 1049 - 1051 (2007/10/02)
7-Acetoxymethyl-4-methylcoumarin (3) on heating with aq.NaOH furnishes 2-(2'-hydroxy-4'-hydroxymethylphenyl)propene (5), which has been transformed in two steps to the naturally occuring oxirane, 2-methyl-2-(2'-hydroxy-4'-hydroxymethylphenyl)oxirane diisobutyrate (14).Selenium dioxide oxidation of 2-(2'-acetoxy-4'-acetoxymethylphenyl)propene (7) yields 2-(2'-acetoxy-4'-acetoxymethylphenyl)prop-2-en-1-al (8) which on reduction with NaBH4 and subsequent saponification furnishes 2-(2'-hydroxy-4'-hydroxymethylphenyl)prop-2-en-1-ol (9).The triol (9) has been transformed in two steps into 2-hydroxymethyl-2-(2'-hydroxy-4'-hydroxymethylphenyl)oxirane triisobutyrate (15).An alternative synthesis of 9 is also described.The preparation of o-isopropenylphenol (5) by the action of aq.NaOH alone, instead of NaOH-ethylene glycol, on the coumarin (3) is significant.This modification provides a conveniant route for the preparation of o-isopropenylphenols in those cases where the use of NaOH-ethylene glycol is not satisfactory.
