scholarly journals The Fries Rearrangement ofbz-Benzoyloxybenzofuran Derivatives and the Synthesis of the Furo Derivatives of 4-Phenyl-2H-chromen-2-one

1978 ◽  
Vol 51 (6) ◽  
pp. 1907-1908 ◽  
Author(s):  
Yoshiyuki Kawase ◽  
Seiji Yamaguchi ◽  
Kumiko Aoyama ◽  
Michiyo Matsuda
Keyword(s):  
Fries Rearrangement ◽  
Derivatives Of

SOME DERIVATIVES OF DIALKOXY-PHTHALIDES

1944 ◽  
Vol 22b (4) ◽  
pp. 115-124 ◽  
Author(s):  
Richard H. F. Manske ◽  
Archie E. Ledingham
Keyword(s):  
Benzoic Acids ◽  
Chloromethyl Group ◽  
Fries Rearrangement ◽  
Derivatives Of

Treatment of certain dialkoxy-benzoic acids was found to yield dialkoxy-phthalides containing a chloromethyl group. The constitutions of a number of these compounds have been elucidated by unambiguous syntheses. Inter alia, it was observed that the Fries rearrangement of 4-acetoxy-3-methoxy-toluene yielded exclusively a m-hydroxy-acetophenone. This appears to be the only recorded case of an exclusive meta-rearrangement. Several intermediate aldehydes and some compounds derived from them are described.

scholarly journals SYNTHESIS OF FLAVANONE-6-CARBOXYLIC ACID DERIVATIVES FROM SALICYLIC ACID DERIVATIVE

2012 ◽  
Vol 12 (1) ◽  
pp. 70-76 ◽  
Author(s):  
Muhammad Idham Darussalam Mardjan ◽  
Retno Ambarwati ◽  
Sabirin Matsjeh ◽  
Tutik Dwi Wahyuningsih ◽  
Winarto Haryadi
Keyword(s):  
Salicylic Acid ◽  
Carboxylic Acid ◽  
Acid Derivative ◽  
Ring Closure ◽  
Hydroxybenzoic Acid ◽  
Fries Rearrangement ◽  
Acetophenone Derivatives ◽  
Ft Ir ◽  
Benzaldehyde Derivatives ◽  
Derivatives Of

Synthesis of flavanone-6-carboxylic acid derivatives had been conducted via the route of chalcone. The synthesis was carried out from salicylic acid derivative, i.e. 4-hydroxybenzoic acid, via esterification, Fries rearrangement, Claisen-Schmidt condensation and 1,4-nucleophilic addition reactions. Structure elucidation of products was performed using FT-IR, 1H-NMR, GC-MS and UV-Vis spectrometers. Reaction of 4-hydroxybenzoic acid with methanol catalyzed with sulfuric acid produced methyl 4-hydroxybenzoate in 87% yield. The acid-catalyzed-acetylation of the product using acetic anhydride gave methyl 4-acetoxybenzoate in 75% yield. Furthermore, solvent-free Fries rearrangement of methyl 4-acetoxybenzoate in the presence of AlCl3 produced 3-acetyl-4-hydroxybenzoic acid as the acetophenone derivatives in 67% yield. Then, Claisen-Schmidt condensation of the acetophenone and benzaldehyde derivatives of p-anisaldehyde and veratraldehyde in basic condition gave 2'-hydroxychalcone-5'-carboxylic acid derivatives  in 81 and 71 % yield, respectively. Finally, the ring closure reaction of the chalcone yielded the corresponding flavanone-6-carboxylic acids in 67 and 59% yield, respectively.

Sign in / Sign up

Export Citation Format

Share Document