2-ethylbenzene-1,3-diol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 629 g. of 2-ethylresorcinol in 1 l. of dioxane were added 530 g. of benzaldehyde and 30 g. of phosphorus oxychloride as a catalyst. The resulting mixture was stirred at room temperature for 24 hours and thereafter poured into 5 l. of a cold water with stirring to give a pale brown powdery resin. poured into 5 l to give a pale brown powdery resin

Conditions: temp:160.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Ethyl-1,3-cyclohexanedione (15 g, 107 mmol), mesitylene (240 mL), and 5% Pd/C (7.8 g) were placed in a flask. The reaction mixture was stirred at 160° C. for two days. Filtration gave a crude product, which was purified by chromatography (EtOAc/Hexane) to give 2-ethyl-3-hydroxy phenol (2.2 g, 15%). Filtration gave a crude product, which was purified by chromatography (EtOAc/Hexane)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: This compounds was synthesised in the same manner as described above. Ethyl resorcinol (0.83 g, 6 mmol), 3,4-dimethoxyphenylacetic acid (0.83 g, 6 mmol), BF3Et2O (4 ml), PCl5 (1.9 g, 9.1 mmol), DMF (5 ml and 10 ml). The precipitate formed was filtered and re-crystallized from methanol to give 3-(3,4-dimethoxy-phenyl)-6-ethyl-7-hydroxy-chromen-4-one as a pale brown solid (1.8 g, 92%); Rf 0.4 cf SM 0.5 ether/petroleum ether [40–60° C.] (50/50). This compounds was synthesised in the same manner The precipitate formed was filtered re-crystallized from methanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: This compounds was synthesised in the same manner as described above. Ethyl resorcinol (0.83 g, 6 mmol), 4-bromophenylacetic acid (1.29 g, 6 mmol), BF3Et2O (5 ml), PCl5 (1.99, 9.1 mmol), DMF (5 ml and 10 ml). The precipitate formed was filtered and re-crystallized from methanol to give 3-(4-bromo-phenyl)-6-ethyl-7-hydroxy-chromen-4-one as a pale pink solid (1.7 g, 82.3%); Rf 0.84 ethyl acetate. This compounds was synthesised in the same manner The precipitate formed was filtered re-crystallized from methanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: This compounds was synthesised in the same manner as described above. Ethyl resorcinol (0.83 g, 6 mmol), phenylacetic acid (0.82 g, 6 mmol), BF3Et2O (3.88 ml, 31.5 mmol), PCl5 (1.88 g, 9 mmol), DMF (4.6 ml and 10 ml). The precipitate formed was filtered and re-crystallized from methanol to give 6-Ethyl-7-hydroxy-3-phenyl-chromen-4-one as a pale brown solid (1.4 g, 87.7%); Rf 0.4 cf SM 0.5 ethyl acetate/hexane (40/60). This compounds was synthesised in the same manner The precipitate formed was filtered re-crystallized from methanol