1-(4-hydroxyphenyl)prop-2-en-1-one

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A mixture of 4-hydroxyphenyl vinyl ketone (c) (1 g), 4′-heptyl-1,1′-biphenyl-4-carboxylic acid (1.8 g), DCC (1.9 g) DMAP (0.1 g) and methylene chloride (30 mL) was stirred at room temperature for 12 hours. The white solid precipitated was filtrated out, and the solvent was evaporated away from the filtrate. The residue was dissolved in ethyl acetate, and washed with aqueous 2 M NaOH solution and then with water. The solvent was evaporated away, and the residue was purified through column chromatography (eluent: toluene) and then through recrystallization (ethanol) to obtain 0.5 g of colorless crystals, compound (1-13-8). The NMR and MS spectra of the compound well support the structure thereof. The white solid precipitated was filtrated out the solvent was evaporated away from the filtrate The residue was dissolved in ethyl acetate washed with aqueous 2 M NaOH solution The solvent was evaporated away the residue was purified through column chromatography (eluent: toluene) through recrystallization (ethanol)

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

Procedure: A mixture of 4-hydroxyphenyl vinyl ketone (c) (1.0 g), 4-pentylbenzoic acid (1.2 g), DCC (1.9 g), DMAP (0.1 g) and methylene chloride (30 mL) was stirred at room temperature for 12 hours. The white solid precipitated was filtrated out, and the solvent was evaporated away from the filtrate. The residue was dissolved in ethyl acetate, and washed with aqueous 2 M NaOH solution and then with water. The residue was purified through column chromatography (eluent: toluene) and then through recrystallization (ethanol) to obtain 0.4 g of colorless crystals, compound (1-5-11). The NMR and MS spectra of the compound well support the structure thereof. The white solid precipitated was filtrated out the solvent was evaporated away from the filtrate The residue was dissolved in ethyl acetate washed with aqueous 2 M NaOH solution The residue was purified through column chromatography (eluent: toluene) through recrystallization (ethanol)

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

Procedure: 2-Chloroethyl 4-methoxyphenyl ketone (b) (69.4 g) was dissolved in methylene chloride (200 mL), to which was added aluminium chloride (130.8 g) little by little. The resulting mixture was heated with a mantle heater for 2 hours under reflux. After the reaction, the reaction liquid was cooled and poured into ice, and the organic phase was extracted out with ethyl acetate (200 mL) and transferred into a separating funnel. The organic phase was washed with water, and then processed with aqueous 2 M NaOH solution to extract out the intended product into the solution. The aqueous alkali solution was acidified with 6 M hydrochloric acid, and then again extracted with ethyl acetate. The solvent was evaporated away under reduced pressure, and the residue was recrystallized from toluene to obtain 37.9 g of colorless crystals, 4-hydroxyphenyl vinyl ketone (c). The resulting mixture was heated with a mantle heater for 2 hours under reflux After the reaction the reaction liquid was cooled poured into ice the organic phase was extracted out with ethyl acetate (200 mL) transferred into a separating funnel The organic phase was washed with water to extract out the intended product into the solution again extracted with ethyl acetate The solvent was evaporated away under reduced pressure the residue was recrystallized from toluene

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

Procedure: 2-Chloroethyl 4-methoxyphenyl ketone (b) (69.4 g) was dissolved in methylene chloride (200 mL), to which was added aluminium chloride (130.8 g) little by little. The resulting mixture was heated with a mantle heater for 2 hours under reflux. After the reaction, the reaction liquid was cooled and poured into ice, and the organic phase was extracted out with ethyl acetate (200 mL) and transferred into a separating funnel. The organic phase was washed with water, and then processed with aqueous 2 M NaOH solution to extract out the intended product into the solution. The aqueous alkali solution was acidified with 6 M hydrochloric acid, and then again extracted with ethyl acetate. The solvent was evaporated away under reduced pressure, and the residue was recrystallized from toluene to obtain 37.9 g of colorless crystals, 4-hydroxyphenyl vinyl ketone (c). The resulting mixture was heated with a mantle heater for 2 hours under reflux After the reaction the reaction liquid was cooled poured into ice the organic phase was extracted out with ethyl acetate (200 mL) transferred into a separating funnel The organic phase was washed with water to extract out the intended product into the solution again extracted with ethyl acetate The solvent was evaporated away under reduced pressure the residue was recrystallized from toluene

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A mixture of iodide 33 (3.1 g, 6.8 mmol), phenol 27 (1.21 g, 8.17 mmol) and K2CO3 (1.033 g, 7.47 mmol) in acetone (75 mL) was refluxed for 6.5 h. The mixture was cooled, filtered and evaporated. The residue was redissolved in CH2Cl2 (170 mL), filtered through Celite and evaporated to give crude 34 (3.2 g, 99%) which was used directly in the next step. 1H NMR (400 MHz, CDCl3) δ 1.28-1.39 (m, 12H), 1.89-2.25 (m, 4H), 2.26-2.48 (m, 1H), 4.05 (t, J=5.7, 2H), 4.12-4.26 (m, 8H), 5.87 (dd, J=10.6, 1.8, 1H), 6.42 (dd, J=16.9, 1.8, 1H), 6.93 (d, J=8.8, 2H), 7.17 (dd, J=17.0, 10.4, 1H), 7.95 (d, J=8.8, 2H). was refluxed for 6.5 h The mixture was cooled filtered evaporated The residue was redissolved in CH2Cl2 (170 mL) filtered through Celite evaporated

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

Procedure: The mixture of 4-hydroxyacetophenone (2.719 g, 20 mmol), paraformaldehyde (2.702 g, 90 mmol) and N-methylanilinium trifluoroacetate (6.603 g, 30 mmol) in 20 mL of anhydrous THF was refluxed for 3.5 h and cooled to room temperature. To the red solution was added 60 mL of diethyl ether and the mixture was vigorously stirred for 15 min. The resultant yellow solution was decanted and residual brown-red sticky mud was repeatedly extracted with 50 mL portions of diethyl ether until it turned into yellow solid. The combined organic extracts were washed with half saturated sodium bicarbonate solution (2×) and the aqueous wash was extracted with ether (2×). The combined organic layers were dried over anhydrous sodium sulfate prior to concentration. Flash chromatography on silica gel with 5:1 hexanes/ethyl acetate as the eluent afforded product 27 (1.21 g, 41%) as a pale yellow solid. 1H NMR (400 MHz, CDCl3): δ 5.89 (dd, J=1.8, 10.6 Hz, 1H), 5.91 (s, 1H), 6.43 (dd, J=1.6, 16.9 Hz, 1H), 6.92 (d, J=8.4 Hz, 2H), 7.17 (dd, J=10.6, 17.2 Hz, 1H), 7.93 (d, J=8.4 Hz, 2H). was refluxed for 3.5 h The resultant yellow solution was decanted residual brown-red sticky mud was repeatedly extracted with 50 mL portions of diethyl ether until it The combined organic extracts were washed with half saturated sodium bicarbonate solution (2×) the aqueous wash was extracted with ether (2×) The combined organic layers were dried over anhydrous sodium sulfate to concentration

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

Procedure: A mixture of 4-hydroxyphenyl vinyl ketone (c) (1 g), 4′-heptyl-1,1′-biphenyl-4-carboxylic acid (1.8 g), DCC (1.9 g) DMAP (0.1 g) and methylene chloride (30 mL) was stirred at room temperature for 12 hours. The white solid precipitated was filtrated out, and the solvent was evaporated away from the filtrate. The residue was dissolved in ethyl acetate, and washed with aqueous 2 M NaOH solution and then with water. The solvent was evaporated away, and the residue was purified through column chromatography (eluent: toluene) and then through recrystallization (ethanol) to obtain 0.5 g of colorless crystals, compound (1-13-8). The NMR and MS spectra of the compound well support the structure thereof. The white solid precipitated was filtrated out the solvent was evaporated away from the filtrate The residue was dissolved in ethyl acetate washed with aqueous 2 M NaOH solution The solvent was evaporated away the residue was purified through column chromatography (eluent: toluene) through recrystallization (ethanol)

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

Procedure: A mixture of 4-hydroxyphenyl vinyl ketone (c) (1.0 g), 4-pentylbenzoic acid (1.2 g), DCC (1.9 g), DMAP (0.1 g) and methylene chloride (30 mL) was stirred at room temperature for 12 hours. The white solid precipitated was filtrated out, and the solvent was evaporated away from the filtrate. The residue was dissolved in ethyl acetate, and washed with aqueous 2 M NaOH solution and then with water. The residue was purified through column chromatography (eluent: toluene) and then through recrystallization (ethanol) to obtain 0.4 g of colorless crystals, compound (1-5-11). The NMR and MS spectra of the compound well support the structure thereof. The white solid precipitated was filtrated out the solvent was evaporated away from the filtrate The residue was dissolved in ethyl acetate washed with aqueous 2 M NaOH solution The residue was purified through column chromatography (eluent: toluene) through recrystallization (ethanol)

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

Procedure: 2-Chloroethyl 4-methoxyphenyl ketone (b) (69.4 g) was dissolved in methylene chloride (200 mL), to which was added aluminium chloride (130.8 g) little by little. The resulting mixture was heated with a mantle heater for 2 hours under reflux. After the reaction, the reaction liquid was cooled and poured into ice, and the organic phase was extracted out with ethyl acetate (200 mL) and transferred into a separating funnel. The organic phase was washed with water, and then processed with aqueous 2 M NaOH solution to extract out the intended product into the solution. The aqueous alkali solution was acidified with 6 M hydrochloric acid, and then again extracted with ethyl acetate. The solvent was evaporated away under reduced pressure, and the residue was recrystallized from toluene to obtain 37.9 g of colorless crystals, 4-hydroxyphenyl vinyl ketone (c). The resulting mixture was heated with a mantle heater for 2 hours under reflux After the reaction the reaction liquid was cooled poured into ice the organic phase was extracted out with ethyl acetate (200 mL) transferred into a separating funnel The organic phase was washed with water to extract out the intended product into the solution again extracted with ethyl acetate The solvent was evaporated away under reduced pressure the residue was recrystallized from toluene