4-hexoxyphenol

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

Procedure: Sodium hydride (2.4 g, 0.1 mol) was suspended in 150 mL dry glyme. Monobenzylhydroquinone (20.0 g, 0.1 mol) was dissolved in 250 mL dry glyme and added dropwise to the sodium hydride suspension with stirring under nitrogen at room temperature. 1-Bromohexane (16.5 g, 0.1 mol) was added dropwise and the reaction mixture was refluxed for 1 day. The reaction product was cooled and the glyme removed under reduced pressure. The residue was dissolved in 300 mL 1:1 ethanol-ethyl acetate and catalytically hydrogenated using 2 g 10% Pd on C and a hydrogen pressure of 500 kPa at room temperature for 4 hours. The catalyst was removed by filtration and the solvent was removed from the filtrate under reduced pressure. The crude product residue was recrystallized from aqueous ethanol to yield 15 g 4-hexyloxyphenol. the reaction mixture was refluxed for 1 day The reaction product was cooled the glyme removed under reduced pressure The residue was dissolved in 300 mL 1:1 ethanol-ethyl acetate The catalyst was removed by filtration the solvent was removed from the filtrate under reduced pressure The crude product residue was recrystallized from aqueous ethanol

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

Procedure: The procedure of Example 1 was followed except that the 4-n-octoxybiphenylcarboxylic acid and 4-(4'-methylheptyloxy)phenol were replaced by 4-(4'-methyloctoxy) biphenylcarboxylic acid and 4-n-hexyloxyphenol and the title compound was obtained.

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

Procedure: 4-(benzyloxy)benzoic acid (20.0 g, 87.6 mmol), 4-(hexyloxy)phenol (17.0 g, 87.6 mmol), N,N′-dicyclohexylcarbodiimide (21.7 g, 105 mmol) and 4-dimethylaminopyridine (535 mg, 4.38 mmol) were dissolved in 300 mL of methylene chloride. The resulting solution was stirred for 3 hours at room temperature. Then, 300 mL of pure water was added thereto, and then the resulting liquid was filtered to remove insoluble matters. Thereafter, the obtained solution was subjected to separation operation, and the resulting methylene chloride solution was washed with a saturated aqueous sodium chloride solution and dried over magnesium sulfate. After methylene chloride was distilled off, the resulting solid matter was washed with methanol. Thereby, a white solid compound, 4-(hexyloxy)phenyl 4-(benzyloxy)benzoate (24.9 g) was obtained. the resulting liquid was filtered to remove insoluble matters Thereafter, the obtained solution was subjected to separation operation the resulting methylene chloride solution was washed with a saturated aqueous sodium chloride solution dried over magnesium sulfate After methylene chloride was distilled off the resulting solid matter was washed with methanol

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

Procedure: 4-(benzyloxy)benzoic acid (20.0 g, 87.6 mmol), 4-(hexyloxy)phenol (17.0 g, 87.6 mmol), N,N′-dicyclohexylcarbodiimide (21.7 g, 105 mmol) and 4-dimethylaminopyridine (535 mg, 4.38 mmol) were dissolved in 300 mL of methylene chloride. The resulting solution was stirred for 3 hours at room temperature. Then, 300 mL of pure water was added thereto, and then the resulting liquid was filtered to remove insoluble matters. Thereafter, the obtained solution was subjected to separation operation, and the resulting methylene chloride solution was washed with a saturated aqueous sodium chloride solution and dried over magnesium sulfate. After methylene chloride was distilled off, the resulting solid matter was washed with methanol. Thereby, a white solid compound, 4-(hexyloxy)phenyl 4-(benzyloxy)benzoate (24.9 g) was obtained. the resulting liquid was filtered to remove insoluble matters Thereafter, the obtained solution was subjected to separation operation the resulting methylene chloride solution was washed with a saturated aqueous sodium chloride solution dried over magnesium sulfate After methylene chloride was distilled off the resulting solid matter was washed with methanol

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

Procedure: In tetrahydrofuran were dissolved 1.0 g of p-octyloxybenzoic acid chloride and 800 mg of p-hexyloxyphenol, and 500 mg of triethylamine was added to the solution and reaction was carried out with stirring overnight. The precipitate was removed by filtration, and the filtrate was concentrated, purified by using a silica gel column and recrystallized from ethanol to obtain 800 mg of 4-hexyloxyphenyl 4-octyloxybenzoate. The phase transition temperatures of the so-obtained compounds are as follows. ##STR142## was added to the solution and reaction The precipitate was removed by filtration the filtrate was concentrated purified recrystallized from ethanol

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

Procedure: The procedure of Example 1 was followed except that the 4-(5'-methyldecyl)benzoic acid and 4-n-octoxyphenol were replaced by 4-(7'-methylundecyl)benzoic acid prepared by reacting 6-methyldecylbromide with 4-methylbenzic acid and 4-n-hexyloxyphenol to thereby give the title compound. prepared

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

Procedure: Sodium hydride (2.4 g, 0.1 mol) was suspended in 150 mL dry glyme. Monobenzylhydroquinone (20.0 g, 0.1 mol) was dissolved in 250 mL dry glyme and added dropwise to the sodium hydride suspension with stirring under nitrogen at room temperature. 1-Bromohexane (16.5 g, 0.1 mol) was added dropwise and the reaction mixture was refluxed for 1 day. The reaction product was cooled and the glyme removed under reduced pressure. The residue was dissolved in 300 mL 1:1 ethanol-ethyl acetate and catalytically hydrogenated using 2 g 10% Pd on C and a hydrogen pressure of 500 kPa at room temperature for 4 hours. The catalyst was removed by filtration and the solvent was removed from the filtrate under reduced pressure. The crude product residue was recrystallized from aqueous ethanol to yield 15 g 4-hexyloxyphenol. the reaction mixture was refluxed for 1 day The reaction product was cooled the glyme removed under reduced pressure The residue was dissolved in 300 mL 1:1 ethanol-ethyl acetate The catalyst was removed by filtration the solvent was removed from the filtrate under reduced pressure The crude product residue was recrystallized from aqueous ethanol

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

Procedure: The procedure of Example 1 was followed except that the 4-n-octoxybiphenylcarboxylic acid and 4-(4'-methylheptyloxy)phenol were replaced by 4-(4'-methyloctoxy) biphenylcarboxylic acid and 4-n-hexyloxyphenol and the title compound was obtained.

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

Procedure: 4-(benzyloxy)benzoic acid (20.0 g, 87.6 mmol), 4-(hexyloxy)phenol (17.0 g, 87.6 mmol), N,N′-dicyclohexylcarbodiimide (21.7 g, 105 mmol) and 4-dimethylaminopyridine (535 mg, 4.38 mmol) were dissolved in 300 mL of methylene chloride. The resulting solution was stirred for 3 hours at room temperature. Then, 300 mL of pure water was added thereto, and then the resulting liquid was filtered to remove insoluble matters. Thereafter, the obtained solution was subjected to separation operation, and the resulting methylene chloride solution was washed with a saturated aqueous sodium chloride solution and dried over magnesium sulfate. After methylene chloride was distilled off, the resulting solid matter was washed with methanol. Thereby, a white solid compound, 4-(hexyloxy)phenyl 4-(benzyloxy)benzoate (24.9 g) was obtained. the resulting liquid was filtered to remove insoluble matters Thereafter, the obtained solution was subjected to separation operation the resulting methylene chloride solution was washed with a saturated aqueous sodium chloride solution dried over magnesium sulfate After methylene chloride was distilled off the resulting solid matter was washed with methanol