64190-69-8

Upstream product

• 53878-05-0 7-bromomethyl-4-methylcoumarin 
• 77878-31-0 7-acetoxymethyl-4-methylcoumarin 
• 78069-60-0 Acetic acid 5-acetoxymethyl-2-(1-acetoxymethyl-vinyl)-phenyl ester 
• 78069-56-4 Isobutyric acid 5-isobutyryloxymethyl-2-(1-isobutyryloxymethyl-vinyl)-phenyl ester 
• 78069-57-5 Acetic acid 5-acetoxymethyl-2-(1-formyl-vinyl)-phenyl ester 
• 78069-58-6 Acetic acid 5-acetoxymethyl-2-(1-bromomethyl-vinyl)-phenyl ester 
• 78069-55-3 2-(2'-acetoxy-4'-acetoxymethylphenyl)propene 

Relevant academic research and scientific papers

Synthesis of Two Naturally Occuring Oxygenated Oxiranes Related to Thymol

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.