4-butylphenol

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:

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

Procedure: Analogously to Example 1, 2.0 g of 2-pentyl-1,2,3,4-tetrahydronaphthalene-6-carboxylic acid are converted into the acid chloride and this is reacted with 1.202 g of p-butylphenol in 5 ml of absolute pyridine. There are obtained 3.0 g of crude p-butylphenyl 2-pentyl-1,2,3,4-tetrahydro-6-naphthoate for purification, is chromatographed on 95 g of silica gel. Elution with hexane/toluene (1:1) yields 2.8 g of substance which is recrystallized from ether/hexane up to constant melting point and clearing point and dried up to constant weight in a high vacuum (0.01 mbar). There are obtained colorless crystals of p-butylphenyl 2-pentyl-1,2,3,4-tetrahydro-6-naphthoate; m.p. 48.1° C., cl.p. 80.7° C.

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

Procedure: Following procedure A, 2-chloro-5-nitropyridine (103 mg, 0.65 mmol, 1.00 eq) and 4-butylphenol (126 mg, 0.84 mmol, 1.29 eq) were dissolved in DMF (2.5 mL). Anhydrous K2CO3 (143 mg, 1.04 mmol, 1.59 eq) was added and the reaction mixture was stirred at room temperature for 6 h. After extraction with Et2O, the crude product was purified by flash column chromatography (SiO2; EtOAc/petrolether 1:100) to afford the title compound as colourless solid (190 mg, 0.70 mmol, quant. yield). Rf=0.33 (EtOAc/PE 1:20). HRMS (ESI) calcd. for C15H17N2O3+ [M+H]+ 273.1234. found: 273.1226. 1H NMR (400 MHz, CDCl3) δ 9.05 (dd, J=2.9, 0.6 Hz, 1H, aromatic H), 8.46 (dd, J=9.1, 2.8 Hz, 1H, aromatic H), 7.32-7.21 (m, 2H, aromatic H), 7.11-7.02 (m, 2H, aromatic H), 7.00 (dd, J=9.0, 0.6 Hz, 1H, aromatic H), 2.69-2.60 (m, 2H, Ar—CH2CH2CH2CH3), 1.70-1.57 (m, 2H, Ar—CH2CH2CH2CH3), 1.39 (dq, J=14.6, 7.3 Hz, 2H, Ar—CH2CH2CH2CH3), 0.95 (t, J=7.3 Hz, 3H, Ar—CH2CH2CH2CH3). 13C NMR (101 MHz, CDCl3) δ 167.27, 150.75, 145.22, 140.86, 140.30, 134.92, 129.91, 121.22, 111.32, 35.21, 33.67, 22.51, 14.08. After extraction with Et2O the crude product was purified by flash column chromatography (SiO2; EtOAc/petrolether 1:100)

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

Procedure: 4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,3-dimethylaniline (50 mg) was added to toluene (5 ml), and triethylamine (0.5 ml), and the mixture was heated under reflux to prepare a solution. A solution of triphosgene (68 mg) in methylene chloride was then added thereto, and the mixture was heated under reflux for 10 min. Next, 4-butylphenol (35 mg) was added thereto, and the mixture was further stirred with heating under reflux for 3 hr. A saturated aqueous sodium bicarbonate solution was added to stop the reaction, and the reaction solution was then extracted with chloroform, followed by washing with a 1 N aqueous hydrochloric acid solution, water, and saturated brine in that order. The extract was dried over sodium sulfate and was then concentrated. The residue was purified on a column using chloroform/methanol to give the title compound (44 mg, yield 55%). the mixture was heated under reflux to prepare a solution the mixture was heated under reflux for 10 min with heating under reflux for 3 hr the reaction the reaction solution was then extracted with chloroform by washing with a 1 N aqueous hydrochloric acid solution, water, and saturated brine in that order The extract was dried over sodium sulfate was then concentrated The residue was purified on a column

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

Procedure: 4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,3-dimethylaniline (50 mg) was added to toluene (5 ml), and triethylamine (0.5 ml), and the mixture was heated under reflux to prepare a solution. A solution of triphosgene (68 mg) in methylene chloride was then added thereto, and the mixture was heated under reflux for 10 min. Next, 4-butylphenol (35 mg) was added thereto, and the mixture was further stirred with heating under reflux for 3 hr. A saturated aqueous sodium bicarbonate solution was added to stop the reaction, and the reaction solution was then extracted with chloroform, followed by washing with a 1 N aqueous hydrochloric acid solution, water, and saturated brine in that order. The extract was dried over sodium sulfate and was then concentrated. The residue was purified on a column using chloroform/methanol to give the title compound (44 mg, yield 55%). the mixture was heated under reflux to prepare a solution the mixture was heated under reflux for 10 min with heating under reflux for 3 hr the reaction the reaction solution was then extracted with chloroform by washing with a 1 N aqueous hydrochloric acid solution, water, and saturated brine in that order The extract was dried over sodium sulfate was then concentrated The residue was purified on a column

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

Procedure: 4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,5-dimethylaniline (50 mg) was added to toluene (5 ml), and triethylamine (0.5 ml), and the mixture was heated under reflux to prepare a solution. A solution of triphosgene (68 mg) in methylene chloride was then added thereto, and the mixture was heated under reflux for 10 min. Next, 4-butylphenol (35 mg) was added thereto, and the mixture was further stirred with heating under reflux for 3 hr. A saturated aqueous sodium bicarbonate solution was added to stop the reaction, and the reaction solution was then extracted with chloroform, followed by washing with a 1 N aqueous hydrochloric acid solution, water, and saturated brine in that order. The extract was dried over sodium sulfate and was then concentrated. The residue was purified on a column using chloroform/methanol to give the title compound (12 mg, yield 15%). the mixture was heated under reflux to prepare a solution the mixture was heated under reflux for 10 min with heating under reflux for 3 hr the reaction the reaction solution was then extracted with chloroform by washing with a 1 N aqueous hydrochloric acid solution, water, and saturated brine in that order The extract was dried over sodium sulfate was then concentrated The residue was purified on a column

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

Procedure: 4-[(6,7-Dimethoxy-4-quinolyl)oxy]aniline (100 mg) was added to toluene (10 ml) and triethylamine (1 ml), and the mixture was heated under reflux to prepare a solution. A solution of triphosgene (151 mg) in methylene chloride was then added thereto, and the mixture was heated under reflux for 10 min. Next, 4-butylphenol (77 mg) was added thereto, and the mixture was further stirred with heating under reflux for 3 hr. A saturated aqueous sodium bicarbonate solution was added to stop the reaction, and the reaction solution was then extracted with chloroform, followed by washing with a 1 N aqueous hydrochloric acid solution, water, and saturated brine in that order. The extract was dried over sodium sulfate and was then concentrated. The residue was purified on a column using chloroform/methanol to give the title compound (130 mg, yield 75%). the mixture was heated under reflux to prepare a solution the mixture was heated under reflux for 10 min with heating under reflux for 3 hr the reaction the reaction solution was then extracted with chloroform by washing with a 1 N aqueous hydrochloric acid solution, water, and saturated brine in that order The extract was dried over sodium sulfate was then concentrated The residue was purified on a column

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

Procedure: A solution of 10 g of 4-n-butylphenol, 10 ml of Ac2O and 8 ml of pyridine is stirred at reflux in 10 ml of dichloromethane. After 2 hours, the medium is cooled to room temperature, diluted with dichloromethane, washed with water, washed with 1M HCl solution, washed with saturated CuSO4 solution, washed with water and dried over MgSO4. After evaporation, 10.8 g of the expected compound are recovered in the form of an oil. washed with water washed with 1M HCl solution washed with saturated CuSO4 solution washed with water dried over MgSO4 After evaporation, 10.8 g of the expected compound are recovered in the form of an oil

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

Procedure: A solution of 10 g of 4-n-butylphenol, 10 ml of Ac2O and 8 ml of pyridine is stirred at reflux in 10 ml of dichloromethane. After 2 hours, the medium is cooled to ambient temperature, diluted in dichloromethane, washed with water, washed with a 1M HCl solution, washed in a saturated CuSO4 solution, washed with water, and dried over MgSO4. After evaporation, 10.8 g of the expected compound are recovered in the form of an oil. washed with water washed with a 1M HCl solution washed in a saturated CuSO4 solution washed with water dried over MgSO4 After evaporation, 10.8 g of the expected compound are recovered in the form of an oil