ethyl 3-(4-hydroxyphenyl)propanoate

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

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

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

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

Procedure: To a solution of ethyl 3-(4-hydroxyphenyl)propionate (940 mg, 4.84 mmol) in anhydrous dimethylformamide (9.4 mL) were added t-butyldimethylsilyl chloride (1.0 g, 6.6 mmol) and imidazole (490 mg, 1.5 mmol) at room temperature, and the mixture was left standing at the same temperature for 14 h. The reaction mixture was directly concentrated, and subjected to silica gel column chromatography (hexane-ethyl acetate 25:1→20:1) to give 1.49 g (quantitative) of the title compound as a solid. the mixture was left The reaction mixture was directly concentrated

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

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

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

Procedure: Under a atmosphere of nitrogen, azodicarboxylic dipiperidide (504 mg, 2.0 mmol) was added at 0-5° C. to a stirred solution of tributylphosphine (404 mg, 2.0 mmol), 3-(4-hydroxy-phenyl)-propionic acid ethyl ester (388 mg, 2.0 mmol) and 3,3-bis-(4-bromophenyl)prop-2-en-1-ol (736 mg, 2.0 mmol) in dry THF (50 ml), the mixture warmed to room temperature, and stirred for 4 h. The reaction mixture was concentrated in vacuo, and added water and ethyl acetate (75 ml each). The aqueous layer was collected and further extracted with ethyl acetate (2×75 ml). The organic layers were combined, washed with water, dried (MgSO4) and evaporated. The crude product was then purified by column chromatography on silica (25% ethylacetane in heptane eluent) to give 1.0 g (92%) of the title compound. The reaction mixture was concentrated in vacuo added water and ethyl acetate (75 ml each) The aqueous layer was collected further extracted with ethyl acetate (2×75 ml) washed with water dried (MgSO4) evaporated The crude product was then purified by column chromatography on silica (25% ethylacetane in heptane eluent)

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

Procedure: To an ice-cooled solution of 3-(p-hydroxyphenyl)-propionic acid (8.3 g, 50.0 mmol) in ethanol (100 mL) was dropwise added thionyl chloride (3.7 mL, 50.7 mmol). The mixture was stirred at room temperature over night, concentrated in vacuo and the residue purified by kugelrohr distillation, to give 9.6 g (99%) of 3-(4-hydroxy-phenyl)-propionic acid ethyl ester as a colourless oil. concentrated in vacuo the residue purified by kugelrohr distillation

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

Procedure: Under argon; to a solution of 3-iodonitrobenzene (3.00 g, 12.0 mmol) in pyridine (15 mL) were added ethyl 3-(4-hydroxyphenyl)propionate (2.81 g, 14.5 mmol), copper oxide (3.35 g, 42.2 mmol), and potassium carbonate (4.16 g, 30.1 mmol), and the resulting solution was heated to reflux for 40 hours. The reaction solution was concentrated under reduced pressure. Water and ethyl acetate were added to the residue, and once insoluble matter had been filtered off, and the filtrate was extracted with ethyl acetate out. The ethyl acetate layer was washed with 1 M hydrochloric acid, water and a saturated sodium bicarbonate solution, and then washed with brine. The ethyl acetate layer was dried over anhydrous magnesium sulfate, evaporated, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=9:1→6:1), to thereby yield 1.12 g of the title compound. the resulting solution was heated to reflux for 40 hours The reaction solution was concentrated under reduced pressure Water and ethyl acetate were added to the residue, and once insoluble matter had been filtered off the filtrate was extracted with ethyl acetate out The ethyl acetate layer was washed with 1 M hydrochloric acid, water a saturated sodium bicarbonate solution, and then washed with brine The ethyl acetate layer was dried over anhydrous magnesium sulfate evaporated the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=9:1→6:1)

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of ethyl 3-(4-hydroxyphenyl)-propionate (6.00 g, 30.9 mmol) in DMF (60 mL) were added 4-fluoronitrobenzene (6.54 g, 46.3 mmol) and potassium carbonate (5.12 g, 37.1 mmol). The resulting reaction solution was stirred for 1 hour at 80° C. To the reaction solution was added water and extracted with ethyl acetate. The resulting ethyl acetate layer was washed with water and then with brine. The ethyl acetate layer was dried over anhydrous magnesium sulfate, evaporated, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1), to thereby yield 9.64 g of the title compound. The resulting reaction solution extracted with ethyl acetate The resulting ethyl acetate layer was washed with water The ethyl acetate layer was dried over anhydrous magnesium sulfate evaporated the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1)

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium hydroxide (98 g) was added to a solution of dimethyl formamide (2,800 mL) of ethyl 3-(4-hydroxyphenyl)propionate (400 g) and stirred at 40° C. for 30 minutes. Formation of a salt could be observed visually. 6-acetoxycyclohexane (515 g) was added and stirred at 80° C. for 7 hours. The reaction mixture was poured into water (2,000 mL) and, toluene was further added and stirred. After separation, the toluene layer was washed with 6N hydrochloric acid, an aqueous saturated solution of sodium carbonate and water successively and then dried over anhydrous magnesium sulfate. The solvent was distilled off from the toluene layer to obtain 709 g of concentrates. Sodium hydroxide (185 g) was dissolved in water (400 mL) to which ethanol (600 mL) and 709 g of the concentrates were added and heated and refluxed for 2 hours. The reaction mixture was concentrated under a reduced pressure by using an evaporator and the resultant concentrates were poured into 6N hydrochloric acid. The obtained slurry was filtered to obtain solids. They were recrystallized from ethanol to obtain (4-(6-hydroxyhexyloxy)phenyl)propionic acid (281 g). Melting point: 109° C. to 112° C. stirred at 80° C. for 7 hours was further added stirred After separation the toluene layer was washed with 6N hydrochloric acid an aqueous saturated solution of sodium carbonate and water successively and then dried over anhydrous magnesium sulfate The solvent was distilled off from the toluene layer to obtain 709 g of concentrates were added heated refluxed for 2 hours The reaction mixture was concentrated under a reduced pressure an evaporator the resultant concentrates were poured into 6N hydrochloric acid The obtained slurry was filtered to obtain solids They were recrystallized from ethanol

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

Procedure: Sulfuric acid (230 g) was dropped under stirring for 10 minutes to an ethanol solution (1500 mL) of 3-(4-hydroxyphenyl)propionic acid (1150 g), and refluxed successively for 5 hours. The reaction mixture was concentrated and the obtained concentrated solution was poured into water (1,000 mL) and stirred with addition of ethyl acetate. After separation of the solution, an ethyl acetate layer was neutralized with an aqueous solution of a saturated sodium carbonate, washed with a small amount of water and then dried over anhydrous magnesium sulfate. Ethyl acetate and unreacted ingredients were distilled off from the ethyl acetate layer to obtain concentrates (1,400 g). The concentrates were purified by distillation under a reduced pressure to obtain ethyl 3-(4-hydroxyphenyl)propionate (1,144 g). The boiling point was 160° C./4.0 hPa. refluxed successively for 5 hours The reaction mixture was concentrated the obtained concentrated solution was poured into water (1,000 mL) After separation of the solution washed with a small amount of water dried over anhydrous magnesium sulfate Ethyl acetate and unreacted ingredients were distilled off from the ethyl acetate layer to obtain concentrates (1,400 g) The concentrates were purified by distillation under a reduced pressure