Studies on Lignin and Related Compounds. LXXXIII. Synthesis of 3-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-2-propanone¹

Synthesis and Characterization of (Z)-5-Arylmethylidene-rhodanines with Photosynthesis-Inhibiting Properties

“…Either commercially available rhodanines or prepared 3-(2-hydroxyethyl)rhodanine [ 24 ] and pyrazine-2–carbaldehyde [ 25 ] were used as starting materials. Most of the compounds were reported previously [ 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 ]. (5 Z )-3-(2-Hydroxyethyl)-5-(2-nitrobenzylidene)-2-thioxo-1,3-thiazolidin-4-one ( 11a ), (5 Z )-3-(2-hydroxyethyl)-5-(3-nitrobenzylidene)-2-thioxo-1,3-thiazolidin-4-one ( 11b ) and (5 Z )-5-(pyrazin-2-ylmethylidene)-2-thioxo-1,3-thiazolidin-4-one ( 15 ) are novel compounds.…”

“…(5Z)-5-(4-Hydroxy-3-methoxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one ( 5 ). Yellow crystalline compound; Yield 75%; Mp 233–234 °C (227–228 °C [ 31 ]); Anal. Calcd.…”

4-Thiazolidinones.

“…For the multistep reaction good overall yields can frequently be obtained. Yields of the homo nitriles from the substituted benzaldehydes are 37-65 per cent for the chloroand bromobenzaldehydes (123) and 62 per cent for 2,4-dimethoxybenzaldehyde (206); of the homo acid or its ester, 73 per cent from furfural (489), 72 per cent from vanillin (247), and 44 per cent from 3-hydroxy-4-methoxybenzaldehyde (288); and of the homo amines, 51 per cent from 3,4-dioxymethylene-5methoxybenzaldehyde (504) and 53 per cent from 1-phenyl-1,2,3-triazole-4-carboxaldehyde (551). Instead of forming the -oximino acid, the thiopyruvic acid has been converted to the phenylhydrazone, which can be reduced to the amino acid by zinc and acetic acid (260).…”

The Ethanolysis of 3-Hydroxy-1-(4-Hydroxy-3-Methoxyphenyl)-2-Propanone in Relation to Lignin Chemistry

“…Paper chromatographic experiments on a preparation kept a year in the laboratory indicated that vanillin was the contaminant. Only minor changes were made in the method of synthesis from vanillin reported by Fisher ancl Hibbert (9). Much time was savecl by acetylating homovanillic acicl by the Chattaway method (6), instead of by boiling for six hours ~v i t h acetic anhydride, and high yields (90%) of pure product were obtained.…”

“…Ethanolysis of the diacetate of VII using the conditions employed on wood yielded the same four propylphenol products, I-IV. A study of the ketol, 3-hydroxy-1-(4-hydroxy-3-methoxypheny1)-2-propanone (V), for final proof that it or its en01 (VI) could yield the propylphenols (I-IV) by ethanolysis was delayed by difficulties in its synthesis which was finally achieved by Fisher and Hibbert (9).…”