139386-33-7

Upstream product

• 146607-46-7 5-benzyloxy-4-formyl-7-methoxy-2-methylbenzofuran 
• 146607-43-4 3-methoxy-4-(2-propynyloxy)benzaldehyde diethyl acetal 
• 5651-83-2 3-methoxy-4-(prop-2-ynyloxy)benzaldehyde 
• 146607-45-6 5-benzyloxy-7-methoxy-2-methylbenzofuran 
• 139386-35-9 5-Formyl-7-methoxy-2-methylbenzofuran 
• 146607-44-5 5-hydroxy-7-methoxy-2-methylbenzofuran 
• 121-33-5 vanillin 

Downstream Products

• 139386-28-0 ethyl (E)-β-(2-hydroxy-3-methoxyphenyl)acrylate 
• 139386-34-8 4-methoxy-2-methyl-7H-furo<3,2-f><1>-benzopyran-7-one 

Relevant academic research and scientific papers

Synthetic studies on naturally occurring coumarins. II. Synthesis of 6,7-dimethoxy- and 7,8-dimethoxy-5-[(E)-3-oxo-1-butenyl]coumarins

In connection with studies on the structure elucidation of the so-called Reisch's coumarin isolated from Toddalia asiatica, syntheses of two coumarins (4 and 5) were accomplished via the routes shown in Charts 2 and 3, respectively. Melting points and NMR data of the synthesized coumarins (4 and 5) and of related coumarins (5-methoxysuberenon, toddalenone, and Reisch's coumarin) are given in Table I, suggesting that so-called Reisch's coumarin might be 4.

A convenient synthesis of a simple coumarin

Reaction of salicylaldehydes (1) with carbethoxymethylenephosphorane in diethylaniline under reflux gave coumarins (3) in excellent yields. Methoxy substituent at C'4 on salicylaldehyde (1) facilitated the formation of coumarin from trans-cinnamate (2), which is first prepared by reaction of 1 with Wittig reagent.