1-(4-羟基-3,5-二甲基苯基)丙-1-one

反应条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 2,6-dimethylphenol (10.5 g, 85.95 mmol), propionic acid (4.64 mL, 86.81 mmol), and trifluoromethanesulfonic acid (59 g) was heated to 80° C. for 48 h, then poured onto ice. The mixture was extracted with chloroform and this organic phase was washed with aqueous bicarbonate and brine. The organic layer was dried and concentrated to a dark orange oily solid. The residue was kugelrohr distilled at 1.5 mm Hg and the following fractions were collected: 23-105° C. (pot temperature), discarded forerun; 105-135° C., 11.2 g (73%) of 2,6-dimethyl-4-propionylphenol as a yellow-white solid which had NMR identical to that of preparation 15. poured onto ice The mixture was extracted with chloroform this organic phase was washed with aqueous bicarbonate and brine The organic layer was dried concentrated to a dark orange oily solid The residue was kugelrohr distilled at 1.5 mm Hg the following fractions were collected 23-105° C. (pot temperature) 105-135° C., 11.2 g (73%) of 2,6-dimethyl-4-propionylphenol as a yellow-white solid which of preparation 15

反应条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 2,6-dimethylphenol (10.5 g, 85.95 mmol), propionic acid (4.64 mL, 86.81 mmol), and trifluoromethanesulfonic acid (59 g) was heated to 80° C. for 48 h, then poured onto ice. The mixture was extracted with chloroform and this organic phase was washed with aqueous bicarbonate and brine. The organic layer was dried and concentrated to a dark orange oily solid. The residue was kugelrohr distilled at 1.5 mm Hg and the following fractions were collected: 23-105° C. (pot temperature), discarded forerun; 105-135° C., 11.2 g (73%) of 2,6-dimethyl-4-propionylphenol as a yellow-white solid which had NMR identical to that of preparation 15. poured onto ice The mixture was extracted with chloroform this organic phase was washed with aqueous bicarbonate and brine The organic layer was dried concentrated to a dark orange oily solid The residue was kugelrohr distilled at 1.5 mm Hg the following fractions were collected 23-105° C. (pot temperature) 105-135° C., 11.2 g (73%) of 2,6-dimethyl-4-propionylphenol as a yellow-white solid which of preparation 15

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 5.1 g of 2,6-dimethyl-4-propionylphenol and 5.0 g of 4-methoxyphenylhydrazine hydrochloride were dispersed in 30 ml of isopropanol, and the dispersion was refluxed for 20 hours in a nitrogen stream. Water was added to the reaction mixture, and the precipitated crystals were collected by filtration. The crystals were dissolved in ethyl acetate, and washed with a 5% aqueous sodium hydroxide solution, water, 2N hydrochloric acid and water. The organic layer was dried, and the solvent was evaporated. Recrystallization of the resulting crude crystals from ethanol-hexane gave 5.8 g of 2-(4-hydroxy-3,5-dimethylphenyl)-5-methoxy-3-methylindole. the dispersion was refluxed for 20 hours in a nitrogen stream the precipitated crystals were collected by filtration The crystals were dissolved in ethyl acetate washed with a 5% aqueous sodium hydroxide solution, water, 2N hydrochloric acid and water The organic layer was dried the solvent was evaporated Recrystallization of the resulting crude crystals from ethanol-hexane

反应条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 2,6-dimethylphenol (10.5 g, 85.95 mmol), propionic acid (4.64 mL, 86.81 mmol), and trifluoromethanesulfonic acid (59 g) was heated to 80° C. for 48 h, then poured onto ice. The mixture was extracted with chloroform and this organic phase was washed with aqueous bicarbonate and brine. The organic layer was dried and concentrated to a dark orange oily solid. The residue was kugelrohr distilled at 1.5 mm Hg and the following fractions were collected: 23-105° C. (pot temperature), discarded forerun; 105-135° C., 11.2 g (73%) of 2,6-dimethyl-4-propionylphenol as a yellow-white solid which had NMR identical to that of preparation 15. poured onto ice The mixture was extracted with chloroform this organic phase was washed with aqueous bicarbonate and brine The organic layer was dried concentrated to a dark orange oily solid The residue was kugelrohr distilled at 1.5 mm Hg the following fractions were collected 23-105° C. (pot temperature) 105-135° C., 11.2 g (73%) of 2,6-dimethyl-4-propionylphenol as a yellow-white solid which of preparation 15

反应条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 2,6-dimethylphenol (10.5 g, 85.95 mmol), propionic acid (4.64 mL, 86.81 mmol), and trifluoromethanesulfonic acid (59 g) was heated to 80° C. for 48 h, then poured onto ice. The mixture was extracted with chloroform and this organic phase was washed with aqueous bicarbonate and brine. The organic layer was dried and concentrated to a dark orange oily solid. The residue was kugelrohr distilled at 1.5 mm Hg and the following fractions were collected: 23-105° C. (pot temperature), discarded forerun; 105-135° C., 11.2 g (73%) of 2,6-dimethyl-4-propionylphenol as a yellow-white solid which had NMR identical to that of preparation 15. poured onto ice The mixture was extracted with chloroform this organic phase was washed with aqueous bicarbonate and brine The organic layer was dried concentrated to a dark orange oily solid The residue was kugelrohr distilled at 1.5 mm Hg the following fractions were collected 23-105° C. (pot temperature) 105-135° C., 11.2 g (73%) of 2,6-dimethyl-4-propionylphenol as a yellow-white solid which of preparation 15