4-octoxybenzaldehyde

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:

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: In a round-bottomed flask fitted with thermometer, reflux condenser and stirrer is placed a mixture of 25 ml. glacial acetic acid and 50 ml methanol and in it is dissolved 2.38 g (0.1 mol) 1,4-diaminoanthraquinone. There is then added 4.68 g (0.2 mol) p-octyloxybenzaldehyde and the mixture is heated at 90° for one hour. The reaction mixture is cooled to about 20°-25° and poured into ice water. The precipitated product is collected and recrystallized from ethylene glycol monomethyl ether or 1:1 methanol water as small purple needles. The crystallization is repeated twice more to obtain 1,4-bis(p-octyloxybenzylidene amino)anthraquinone m.b. 280° (dec) having absorption spectra in visual and infra red ranges as shown in FIGS. 9, 10 and 11 and of sufficient purity for use in guest-host combinations. Analysis: Calculated for C44H54N2O4 ; 78.3%C, 8.06%H, 4.15%N: found 77.61%C, 7.46%H, 4.18%N. In a round-bottomed flask fitted with thermometer reflux condenser and stirrer a mixture of 25 ml the mixture is heated at 90° for one hour The reaction mixture is cooled to about 20°-25° The precipitated product is collected recrystallized from ethylene glycol monomethyl ether or 1:1 methanol water as small purple needles The crystallization

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

Procedure: In a round-bottomed flask fitted with thermometer, reflux condenser and stirrer is placed a mixture of 25 ml. glacial acetic acid and 50 ml methanol and in it is dissolved 2.38 g (0.1 mol) 1,4-diaminoanthraquinone. There is then added 4.68 g (0.2 mol) p-octyloxybenzaldehyde and the mixture is heated at 90° for one hour. The reaction mixture is cooled to about 20°-25° and poured into ice water. The precipitated product is collected and recrystallized from ethylene glycol monomethyl ether or 1:1 methanol water as small purple needles. The crystallization is repeated twice more to obtain 1,4-bis(p-octyloxybenzylidene amino)anthraquinone m.b. 280° (dec) having absorption spectra in visual and infra red ranges as shown in FIGS. 9, 10 and 11 and of sufficient purity for use in guest-host combinations. Analysis: Calculated for C44H54N2O4 ; 78.3%C, 8.06%H, 4.15%N: found 77.61%C, 7.46%H, 4.18%N. In a round-bottomed flask fitted with thermometer reflux condenser and stirrer a mixture of 25 ml the mixture is heated at 90° for one hour The reaction mixture is cooled to about 20°-25° The precipitated product is collected recrystallized from ethylene glycol monomethyl ether or 1:1 methanol water as small purple needles The crystallization

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

Procedure: In a round-bottomed flask fitted with thermometer, reflux condenser and stirrer is placed a mixture of 25 ml. glacial acetic acid and 50 ml methanol and in it is dissolved 2.38 g (0.1 mol) 1,4-diaminoanthraquinone. There is taken added 4.68 g (0.2 mol) p-octyloxybenzaldehyde and the mixture is heated at 90° for one hour. The reaction mixture is cooled to about 20°-25° and poured into ice water. The precipitated product is collected and recrystallized from ethylene glycol monomethyl ether or 1:1 methanol water as small purple needles. The crystallization is repeated twice more to obtain 1,4-bis(p-octyloxybenzylidene amino)anthraquinone m.p. 280° C. (dec) having absorption spectra in visual and infra red ranges as shown in FIGS. 9, 10, and 11 and of sufficient purity for use in guest-host combinations. In a round-bottomed flask fitted with thermometer reflux condenser and stirrer a mixture of 25 ml the mixture is heated at 90° for one hour The reaction mixture is cooled to about 20°-25° The precipitated product is collected recrystallized from ethylene glycol monomethyl ether or 1:1 methanol water as small purple needles The crystallization

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

Procedure: To a suspension of lithium aluminum hydride (4.05 g) in tetrahydrofuran (475 ml) was added dropwise a solution of 4-octyloxybenzaldehyde (25 g) in tetrahydrofuran (25 ml) at 55°-60° C. The reaction mixture was stirred under reflux for 1 hour. Thereto, sodium fluoride (35.84 g) and water (11.52 ml) were added under ice-cooling. The mixture was stirred for 30 minutes, and filtered. The filtrate was evaporated in vacuo to give 4-octyloxybenzyl alcohol (25.1 g) as crystals. under reflux for 1 hour cooling The mixture was stirred for 30 minutes filtered The filtrate was evaporated in vacuo

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

Procedure: Methoxymethyl triphenylphosphonium chloride of 34.28 g was suspended in anhydrous ether of 190 ml, and potassium t-butoxide of 11.22 g was added thereto. A solution prepared by dissolving 4-n-octyloxybenzaldehyde of 22.26 g in anhydrous ether of 110 ml was added thereto, and the solution was stirred at room temperature for 12 hours. Resulting triphenylphosphine oxide was removed by filtration, and the filtrate was poured into ice and water of 300 ml. An ether layer was separated and washed with water, followed by drying the ether layer with anhydrous sodium sulfate. Then, ether was distilled off to obtain crude (4'-n-octyloxyphenyl)-2-methoxyethylene. Further, the crude product was refined by distillation under reduced pressure to obtain (4'-n-octyloxyphenyl)-2-methoxyethylene of 25.4 g. Next, a mixed solution of triethyl orthoformate of 240 g and boron trifluoride ethyl ether complex salt of 6.53 g was cooled down to 0°C., and (4'-n-octyloxyphenyl)-2-methoxyethylene of 25.39 g was added thereto. Then, after stirring the solution at room temperature for 12 hours, toluene of 200 ml and a 10 weight % sodium hydrogencarbonate aqueous solution of 150 ml were added and mixed, and then a toluene layer was separated. The toluene layer was dried with anhydrous sodium sulfate, and then toluene was distilled off to obtain 4-n-octyloxyphenyl malonotetraethyl acetal. This 4-n-octyloxyphenyl malonotetraethyl acetal of 21.2 g was added to water of 12 ml and p-tolenesulfonic acid of 0.05 g, and the reaction was carried out at 80° C. for 3 hours. After cooling the solution down to room temperature, sodium carbonate of 0.52 g was added for neutralization, and then the product was extracted with toluene. The extract was washed with a 10 weight % sodium hydroxide aqueous solution and further washed with water. Then, a toluene layer was separated and dried with anhydrous sodium sulfate, and toluene was distilled off to obtain α-(4-n-octyloxyphenyl)-β-ethoxyacrolein of 16.62 g. was added A solution prepared was added Resulting triphenylphosphine oxide was removed by filtration the filtrate was poured into ice and water of 300 ml An ether layer was separated washed with water by drying the ether layer with anhydrous sodium sulfate Then, ether was distilled off to obtain crude (4'-n-octyloxyphenyl)-2-methoxyethylene Further, the crude product was refined by distillation under reduced pressure