109386-29-0

Upstream product

• 150-19-6 O-methylresorcine 
• 943-89-5 (E)-3-(4-methoxyphenyl)acrylic acid 
• 830-09-1 3-(4'-methoxyphenyl)propenoic acid 
• 24393-56-4 ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate 
• 2227-57-8 3-(4-methoxyphenyl)propynoic acid 
• 108-46-3 recorcinol 

Downstream Products

• 23982-32-3 7-methoxy-4-(4-methoxyphenyl)coumarin 
• 66869-42-9 4-(4-Hydroxyphenyl)-7-hydroxycoumarin 

Relevant academic research and scientific papers

Synthesis of substituted (±)-3,4-dihydrocoumarins using H-Y zeolite

Synthesis of substituted (±)-3,4 Dihydrocoumarins were prepared with the reaction between substituted cinnamic acid and phenol catalysed by eco- friendly solid-acid catalyst H-Y zeolite involving esterification followed by ring closure.

Hexafluoroisopropanol and Acetyl Chloride Promoted Catalytic Hydroarylation with Phenols

We report a catalytic hydroarylation method to convert phenols to dihydrocoumarins in hexafluoroisopropanol (HFIP) using acid generated from sub-stoichiometric amounts of acetyl chloride as catalyst. Attractive elements include easy set-up and isolation, and applicability to a range of phenols including natural product substrates.

Antioxidant and antitumor activities of 4-arylcoumarins and 4-aryl-3,4-dihydrocoumarins

Five 4-arylcoumarins (1c-g) and twelve 3,4-dihydro-4-arylcoumarins (2a-l) were synthesized and tested for antioxidant activity, antitumor activity, toxicity and structure-activity relationships analysis. 4-Arylcoumarins and 3,4-dihydro-4-arylcoumarins tha

Synthesis and NMR of 4-Aryl-3,4-dihydrocoumarins and 4-arylcoumarins

This paper described the synthesis and 1H and 13C NMR chemical shifts of a series of 4-aryl-3,4-dihydrocoumarin and 4-arylcoumarin derivatives based on a combination of 1H and 13C NMR, HSQC and HMBC experiments.

Synthesis and antimicrobial activities of 4-aryl-3,4-dihydrocoumarins and 4-arylcoumarins

A new series of 4-aryl-3,4-dihydrocoumarins and 4-arylcoumarins were synthesized by the reaction of substituted cinnamic acids and 3-arylpropiolic acid with the corresponding phenols. These compounds were evaluated for antibacterial activity in vitro. The

Short synthesis of cytotoxic 4-arylcoumarins

A short synthesis of cytotoxic 4-arylcoumarins via condensation of phenols with cinnamic acids in the presence of CF3COOH, followed by dehydrogenation with DDQ, is described. Copyright Taylor & Francis Group, LLC.

A convenient synthesis of dihydrocoumarins from phenols and cinnamic acid derivatives

A facile procedure for synthesis of dihydrocoumarin derivatives was described. Although the yield of the products in the reaction of phenols with acrylates in trifluoroacetic acid in the presence of Pd(OAc)2 giving coumarins was found to be very low, dihydrocoumarin derivatives were obtained in good to high yields in the absence of Pd(OAc)2 when ethyl cinnamates bearing electron-donating groups were employed in this reaction.

Synthesis and structural elucidation of (±)-3,4-dihydrocoumarins by 2D- NOESY spectrum

(±)-3,4-Dihydrocoumarins have been synthesized in high yield and the structures are confirmed by 2D-NOESY spectrum.

Condensation of Phenols and Cinnamic Acids in Presence of Polyphosphoric Acid: A Novel Biogenetic-type Oxidative Self-cyclisation of p-Methoxycinnamic Acid to 7-Methoxycoumarin

The course of PPA condensation/cyclisation of different phenols and cinnamic acids has been found to depend upon the nature of the substrate, stoichiometry, composition of PPA, and reaction condition.Condensation of phloroglucinol (50-70 deg C, 1 hr) with cinnamic acid in the presence of PPA leads to pinocembrin (I) (50percent) and 5-hydroxy-4,8-diphenyl-3,4,6,7-tetrahydro2H,6H-benzodipyran-2,6-dione (II) (14percent).This condensation reaction when carried out with resorcinol for 2 hr furnishes 7-hydroxyflavanone (III) (60percent).Condensation of resorcinol monomethyl ether affords 2'-hydroxy-4'-methoxychalcone (IV) (12percent) and 4'-hydroxy-2'-methoxychalcone (V) (40percent), but no flavanone derivative.Reaction of p-methoxycinnamic acid (in xylene), in the presence of PPA and resorcinol, however, yields 7-hydroxy-4-(4'-methoxyphenyl)-3,4-dihydrocoumarin (VI) (56percent); with resorcinol monomethyl ether the corresponding 7-methoxy derivative (VII) (44percent) is obtained.Further, p-methoxycinnamic acid undergoes self-condensation in the presence of 0.5 mol equiv of phloroglucinol or resorcinol to give p-methoxycinnamic anhydride (VIII) (only 4percent) or bis(methoxybenzal)acetone (IX) (50percent).Interestingly, in the presence of resorcinol monomethyl ether (0.5 mol equiv, 4hr) p-methoxycinnamic acid undergoes biogenetic-type oxidative self-cyclisation to form 7-methoxycoumarin (X) (80percent).A plausible mechanism for the formation of X has been suggested.