2-(4-methylphenyl)acetyl chloride

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

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

Procedure: Phosphorus pentachloride (1.lg, 0.0053 mol) was added to 4-methylphenylacetic acid (0.76g, 0.0051 mol) and the mixture was allowed to react by heating at about 80° C. POCl3 and excess phosphorus pentachloride were completely removed by evaporation in vacuo to obtain 4-methylphenylacetyl chloride. This chloride was dissolved in toluene (10 ml) and to the mixture were added S-(-)-α(4-n-heptyloxyphenyl)ethyl alcohol (1.0g, 0.0042 mol) and pyridine (1 ml, a dehydrochlorinating agent). The mixture was permitted to stand for 10 hours at room temperature, warmed at 60° C. and maintained as such for 3 hours, and then cooled. The resulting mixture was added to diluted hydrochloric acid and the resultant was extracted with ether. The ether layer was washed with an aqueous solution of NaHCO3 and then with water, and dried over Na2SO4. The ether was distilled off and the residue was purified by means of a column chromatography (solvent : chloroform) and the resultant was recrystallized from ethanol to obtain the objective compound of α-(4-n-heptyloxyphenyl)ethyl 4-methylphenylacetate. The infrared spectrum of said compound is shown in FIG. 4. This compound did not show any liquid crystalline phase and it was a liquid at room temperature. The angle of rotation [α]25D of the compound was -13.1° (solvent : chloroform). to react POCl3 and excess phosphorus pentachloride were completely removed by evaporation in vacuo

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

Procedure: Phosphorus pentachloride (1.lg, 0.0053 mol) was added to 4-methylphenylacetic acid (0.76g, 0.0051 mol) and the mixture was allowed to react by heating at about 80° C. POCl3 and excess phosphorus pentachloride were completely removed by evaporation in vacuo to obtain 4-methylphenylacetyl chloride. This chloride was dissolved in toluene (10 ml) and to the mixture were added S-(-)-α(4-n-heptyloxyphenyl)ethyl alcohol (1.0g, 0.0042 mol) and pyridine (1 ml, a dehydrochlorinating agent). The mixture was permitted to stand for 10 hours at room temperature, warmed at 60° C. and maintained as such for 3 hours, and then cooled. The resulting mixture was added to diluted hydrochloric acid and the resultant was extracted with ether. The ether layer was washed with an aqueous solution of NaHCO3 and then with water, and dried over Na2SO4. The ether was distilled off and the residue was purified by means of a column chromatography (solvent : chloroform) and the resultant was recrystallized from ethanol to obtain the objective compound of α-(4-n-heptyloxyphenyl)ethyl 4-methylphenylacetate. The infrared spectrum of said compound is shown in FIG. 4. This compound did not show any liquid crystalline phase and it was a liquid at room temperature. The angle of rotation [α]25D of the compound was -13.1° (solvent : chloroform). to react POCl3 and excess phosphorus pentachloride were completely removed by evaporation in vacuo

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

Procedure: The N-formyl-2-(p-methylphenyl)-acetamide (m.p. 144°-146°C.) used as starting material was prepared from formamide and 4-methyl-phenyl-acetyl chloride in the manner described in Example 2 for the preparation of N-formyl-N-methyl-2-phenyl-acetamide.

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

Procedure: Starting from 400 g (1.32 mmol) of 5-amino-1-[1-(1-hydroxy-ethyl)-4-phenyl-butyl]-1H-pyrazole-4-carboxamide and 578 mg (3.44 mmol) of 4-methylphenylacetylchloride, the title compound is prepared analogously to the protocol of Example 13. This gives 117 mg (21%) of the diastereomer which elutes more rapidly, M.p.: 133° C., and 75 mg (13.6%) of the diastereomer which elutes more slowly, M.p.: 136° C.

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

Procedure: Phosphorus pentachloride (1.lg, 0.0053 mol) was added to 4-methylphenylacetic acid (0.76g, 0.0051 mol) and the mixture was allowed to react by heating at about 80° C. POCl3 and excess phosphorus pentachloride were completely removed by evaporation in vacuo to obtain 4-methylphenylacetyl chloride. This chloride was dissolved in toluene (10 ml) and to the mixture were added S-(-)-α(4-n-heptyloxyphenyl)ethyl alcohol (1.0g, 0.0042 mol) and pyridine (1 ml, a dehydrochlorinating agent). The mixture was permitted to stand for 10 hours at room temperature, warmed at 60° C. and maintained as such for 3 hours, and then cooled. The resulting mixture was added to diluted hydrochloric acid and the resultant was extracted with ether. The ether layer was washed with an aqueous solution of NaHCO3 and then with water, and dried over Na2SO4. The ether was distilled off and the residue was purified by means of a column chromatography (solvent : chloroform) and the resultant was recrystallized from ethanol to obtain the objective compound of α-(4-n-heptyloxyphenyl)ethyl 4-methylphenylacetate. The infrared spectrum of said compound is shown in FIG. 4. This compound did not show any liquid crystalline phase and it was a liquid at room temperature. The angle of rotation [α]25D of the compound was -13.1° (solvent : chloroform). to react POCl3 and excess phosphorus pentachloride were completely removed by evaporation in vacuo

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

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

Procedure: 2.30 g (8.48 mmol) of crude 2-(4-benzyloxy-3-methoxyphenyl)-1-methylethylamine, 1.03 g (10.2 mmol) of triethylamine and 25 ml of tetrahydrofuran were mixed and cooled to about 0° C. and then 1.42 g (8.48 mmol) of (4-methylphenyl)acetyl chloride was added dropwise thereto. The mixture was stirred at 0° C. for 30 minutes and further at room temperature for 2 hours. Water was added to the reaction mixture, which was followed by extracted with ethyl acetate, washed with 5% hydrochloric acid and saturated brine subsequently, dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was washed with hexane and dried to give 2.40 g of N-[2-(4-benzyloxy-3-methoxyphenyl)-1-methylethyl]-2-(4-methylphenyl) acetamide. by extracted with ethyl acetate washed with 5% hydrochloric acid and saturated brine subsequently dried over anhydrous magnesium sulfate the solvent was distilled off under reduced pressure The residue was washed with hexane dried

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

Procedure: 15.26 g (59.3 mmol) of crude 2-(3-methoxy-4-benzyloxyphenyl)ethylamine, 9.09 g (89.0 mmol) of triethylamine and 100 ml of tetrahydrofuran were mixed and cooled to about 0° C. and then 5.44 g (32.28 mmol) of (4-methylphenyl)acetyl chloride was added dropwise thereto. The mixture was stirred at 0° C. for 30 minutes and further at room temperature for 3 hours. Water was added to the reaction mixture, which was followed by extracted with ethyl acetate, washed with 5% hydrochloric acid and saturated brine subsequently, dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was washed with hexane and dried to give 19.48 g of N-[2-(4-benzyloxy-3-methoxyphenyl)ethyl]-2-(4-methylphenyl)acetamide. by extracted with ethyl acetate washed with 5% hydrochloric acid and saturated brine subsequently dried over anhydrous magnesium sulfate the solvent was distilled off under reduced pressure The residue was washed with hexane dried

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

Procedure: A solution of 4-methylphenylacetyl chloride (1.69 g, 10 mmole) in dichloromethane (20 ml) was treated with a suspension of sulphur trioxide--dioxane complex (15 mmole) in dichloromethane. The mixture was stirred at room temperature for eighteen hours and evaporated. evaporated

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

Procedure: By a procedure similar to that of example 1.115.1, starting from 4-methylphenylacetyl chloride and ethyl N-phenyl-3-aminopropionate, ethyl 3-[2-(4-methylphenyl)-N-phenylacetamido]propanoate was obtained as yellowish oil.

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

Procedure: The N-formyl-2-(p-methylphenyl)-acetamide (m.p. 144°-146°C.) used as starting material was prepared from formamide and 4-methyl-phenyl-acetyl chloride in the manner described in Example 2 for the preparation of N-formyl-N-methyl-2-phenyl-acetamide.