4-octylphenol

Conditions: temp:98.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The procedure described in Example 4 was followed, replacing the phenol (48 g) by 4-octylphenol (105 g 0.5 mole). During addition of the paraformaldehyde, the internal temperature was maintained at 95°-98° C. and the reaction mixture was stirred at 98° C. for a further hour. In other respects, the conditions were as described in Example 4. The product, 5-octylsalicylaldehyde, was obtained in 85% yield. the internal temperature was maintained at 95°-98° C.

Conditions: temp:98.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The procedure described in Example 4 was followed, replacing the phenol (48 g) by 4-octylphenol (105 g 0.5 mole). During addition of the paraformaldehyde, the internal temperature was maintained at 95°-98° C. and the reaction mixture was stirred at 98° C. for a further hour. In other respects, the conditions were as described in Example 4. The product, 5-octylsalicylaldehyde, was obtained in 85% yield. the internal temperature was maintained at 95°-98° C.

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

Procedure: A mixture of 4-octyl phenol (0.15 g, 0.73 mmol), CF3CO2Ag (0.25 g, 1 mmol) and I2 (0.185 g, 0.73 mmol) in CH2Cl2 (10 ml) was stirred for 0.5 h at 0, then for 0.5 h at room temperature. The solution was filtered through Celite bead and washed with CH2Cl2 (30 ml). The filtrates were evaporated to dryness to give the title compound (0.21 g, 87%) as fawn oil. 1H NMR (CDCl3) 7.32 (d, 1H, J=8.34 Hz); 7.28 (d, 1H, J=1.26 Hz); 6.98 (dd, 1H, 8.37, 1.71 Hz); 6.62 (s, 1H); 4.69 (t, 2H, J=5.88 Hz); 3.62-3.38 (m, 4H); 2.59 (t, 2H, J=7.29 Hz); 1.56-1.51 (m, 2H); 1.34-1.2 (m, 10H); 0.81 (t, 3H, J=6.48 Hz). for 0.5 h at room temperature The solution was filtered through Celite bead washed with CH2Cl2 (30 ml) The filtrates were evaporated to dryness

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

Procedure: (2S)-3-[4-(3-Bromo-propoxy)-phenyl]-2-methoxy-propionic acid ethyl ester from Example 173, Step A was treated with 4-Octyl-phenol under the Standard Procedure J. The compound thus obtained was allowed to react under Standard hydrolysis procedure C (NaOH) to give the title compound. MS(ES) for C27H38O5 [M+Na]+: 466. The compound thus obtained

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

Procedure: (2S)-3-[4-(3-Bromo-propoxy)-phenyl]-2-methoxy-propionic acid ethyl ester from Example 173, Step A was treated with 4-Octyl-phenol under the Standard Procedure J. The compound thus obtained was allowed to react under Standard hydrolysis procedure C (NaOH) to give the title compound. MS(ES) for C27H38O5 [M+Na]+: 466. The compound thus obtained

Conditions: temp:98.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The procedure described in Example 4 was followed, replacing the phenol (48 g) by 4-octylphenol (105 g 0.5 mole). During addition of the paraformaldehyde, the internal temperature was maintained at 95°-98° C. and the reaction mixture was stirred at 98° C. for a further hour. In other respects, the conditions were as described in Example 4. The product, 5-octylsalicylaldehyde, was obtained in 85% yield. the internal temperature was maintained at 95°-98° C.

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

Procedure: 5-octylsalicylaldehyde was prepared as follows: p-octyl phenol (20.6 g) was dissolved in dry methylene chloride (400 cm3). The solution was cooled in an ice bath, stirred and treated carefully with titanium tetrachloride (44 cm3). 1,1-Dichloromethyl methyl ether (30 cm3) was then added dropwise to the cooled stirred solution. After the addition was complete, the temperature was raised to 40° C. and stirring continued for a further 15 minutes. The mixture was then poured into crushed ice (500 g) and the organic layer extracted with ether. The ethereal solution was washed several times with water, dried over anhydrous sodium sulpate and evaporated. The oily residue was purified by fractional distillation under vacuum to give 5-octylsalicylaldehyde as a colourless liquid which solidified at 30° C. 5-octylsalicylaldehyde was prepared The solution was cooled in an ice bath stirred solution After the addition stirring The mixture was then poured the organic layer extracted with ether The ethereal solution was washed several times with water dried over anhydrous sodium sulpate evaporated The oily residue was purified by fractional distillation under vacuum

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

Procedure: 5-octylsalicylaldehyde was prepared as follows: p-octyl phenol (20.6 g) was dissolved in dry methylene chloride (400 cm3). The solution was cooled in an ice bath, stirred and treated carefully with titanium tetrachloride (44 cm3). 1,1-Dichloromethyl methyl ether (30 cm3) was then added dropwise to the cooled stirred solution. After the addition was complete, the temperature was raised to 40° C. and stirring continued for a further 15 minutes. The mixture was then poured into crushed ice (500 g) and the organic layer extracted with ether. The ethereal solution was washed several times with water, dried over anhydrous sodium sulpate and evaporated. The oily residue was purified by fractional distillation under vacuum to give 5-octylsalicylaldehyde as a colourless liquid which solidified at 30° C. 5-octylsalicylaldehyde was prepared The solution was cooled in an ice bath stirred solution After the addition stirring The mixture was then poured the organic layer extracted with ether The ethereal solution was washed several times with water dried over anhydrous sodium sulpate evaporated The oily residue was purified by fractional distillation under vacuum

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

Procedure: 4.1 g of 4-n-octylphenol and 1.6 g of pyridine are dissolved in 10 ml of toluene, the solution is warmed to 100°, 5.0 g of 4-(trans-3-n-propylcyclopentyl)benzoyl chloride (cf. Example 2) are added dropwise, and the mixture is left to react for 3 hours. The pyridine hydrochloride is subsequently filtered off under suction, and the filtrate is washed with water, dried and freed from solvent in vacuo. After crystallization of the residue from petroleum ether, 4-octylphenyl 4-(trans-3-propylcyclopentyl)-benzoate is obtained; m.p. 36°, c.p. 40.7°. the solution is warmed to 100° the mixture is left to react for 3 hours The pyridine hydrochloride is subsequently filtered off under suction the filtrate is washed with water dried After crystallization of the residue from petroleum ether

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

Procedure: 4.1 g of 4-n-octylphenol and 1.6 g of pyridine are dissolved in 10 ml of toluene, the solution is warmed to 100°, 5.0 g of 4-(trans-3-n-propylcyclopentyl)benzoyl chloride (cf. Example 2) are added dropwise, and the mixture is left to react for 3 hours. The pyridine hydrochloride is subsequently filtered off under suction, and the filtrate is washed with water, dried and freed from solvent in vacuo. After crystallization of the residue from petroleum ether, 4-octylphenyl 4-(trans-3-propylcyclopentyl)-benzoate is obtained; m.p. 36°, c.p. 40.7°. the solution is warmed to 100° the mixture is left to react for 3 hours The pyridine hydrochloride is subsequently filtered off under suction the filtrate is washed with water dried After crystallization of the residue from petroleum ether

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4-octyl phenol (0.15 g, 0.73 mmol), CF3CO2Ag (0.25 g, 1 mmol) and I2 (0.185 g, 0.73 mmol) in CH2Cl2 (10 ml) was stirred for 0.5 h at 0° C., then for 0.5 h at room temperature. The solution was filtered through Celite bead and washed with CH2Cl2 (30 ml). The filtrates were evaporated to dryness to give the title compound (0.21 g, 87%) as fawn oil. 1H NMR (CDCl3) 7.32 (d, 1H, J=8.34 Hz); 7.28 (d, 1H, J=1.26 Hz); 6.98 (dd, 1H, 8.37, 1.71 Hz); 6.62 (s, 1H); 4.69 (t, 2H, J=5.88 Hz); 3.62-3.38 (m, 4H); 2.59 (t, 2H, J=7.29 Hz); 1.56-1.51 (m, 2H); 1.34-1.2 (m, 10H); 0.81 (t, 3H, J=6.48 Hz). for 0.5 h at room temperature The solution was filtered through Celite bead washed with CH2Cl2 (30 ml) The filtrates were evaporated to dryness

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

Procedure: To a solution of 2.06 g (10 mmol) of 4-octylphenol in 50 mL of THF was added 0.85 g (15 mmol) of powdered KOH and 3.98 g (15 mmol) of 18-crown-6. The solution was heated to 50° C. for 15 minutes, whereupon 2.8 g (15 mmol) of methyl 4,4-diethoxy-2-butynoate was added. The mixture was stirred for 30 minutes, then allowed to cool to room temperature. The solution was then poured into water, and extracted 3 times with 40 mL of ethyl acetate. The organic layers were combined, dried (MgSO4) and concentrated. The crude oil was subjected to column chromatography on SiO2. Elution with 20% ethyl acetate-hexane yielded 2.1 g (54%) of an oil, used in the next step without further purification. was added extracted 3 times with 40 mL of ethyl acetate dried (MgSO4) concentrated Elution with 20% ethyl acetate-hexane