9,10-bis(chloromethyl)anthracene

Conditions: temp:-15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: That is, 2.06 g (27.0 mmol) of N-methylethanolamine was dissolved in 90 ml of anhydrous DMF in a 200 ml three-necked flask. Then, the resulting solution was cooled to −15° C. and to this, 1.08 g (27 mmol) of a 60% solution of NaH was added over 0.5 hours. After addition, the mixed solution was stirred at −15° C. for 1 hour. Then, 3.00 g (13.5 mmol) of 9,10-bis(chloromethyl)anthracene (1) was added gradually in a crystalline state. The resulting mixture was heated to −10° C. after a lapse of one hour from the completion of this addition and stirred over one night. After the completion of a reaction, DMF was distilled off under a reduced pressure, and the residue was dissolved in 200 ml of methylene chloride and insoluble matter was filtered out. 50 ml of water was added to this, and TFA was added while stirring until the pH of the solution becomes acid. After leaving at rest for 15 minutes, the solution was separated into two layers. A water phase was concentrated by repeating this operation two times and then the water phase was freeze-dried to obtain 2.43 g of quaternary anthracene salt 2 at a yield of 33%. After addition The resulting mixture was heated to −10° C. after a lapse of one hour from the completion of this addition stirred over one night was distilled off under a reduced pressure the residue was dissolved in 200 ml of methylene chloride insoluble matter was filtered out 50 ml of water was added to this, and TFA was added while stirring until the pH of the solution After leaving at rest for 15 minutes the solution was separated into two layers A water phase was concentrated the water phase was freeze-dried

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

Procedure: 1.0 g (0.0036 mol) of 9,10-dichloromethylanthracene (0.0036 mol) is refluxed for 20 minutes with 15 g of 2-dimethylaminoethylamine. The reaction mixture is added to water and the precipitate collected by filtration. The dried solid is then recrystallised from ethyl acetate to yield 0.5 g of the title compound as yellow crystals, m.p. 58°-60° C.; λmax (distilled water) (E/cm/M) 248 nm (51760), 372 nm (9030), 392 nm (8305). the precipitate collected by filtration The dried solid is then recrystallised from ethyl acetate

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

Procedure: 1.0 g (0.0036 mol) of 9,10-dichloromethylanthracene (0.0036 mol) is refluxed for 20 minutes with 15 g of 2-dimethylaminoethylamine. The reaction mixture is added to water and the precipitate collected by filtration. The dried solid is then recrystallised from ethyl acetate to yield 0.5 g of the title compound as yellow crystals, m.p. 58°-60° C.; λmax (distilled water) (E/cm/M) 248 nm (51760), 372 nm (9030), 392 nm (8305). the precipitate collected by filtration The dried solid is then recrystallised from ethyl acetate

Conditions: temp:-15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: That is, 2.06 g (27.0 mmol) of N-methylethanolamine was dissolved in 90 ml of anhydrous DMF in a 200 ml three-necked flask. Then, the resulting solution was cooled to −15° C. and to this, 1.08 g (27 mmol) of a 60% solution of NaH was added over 0.5 hours. After addition, the mixed solution was stirred at −15° C. for 1 hour. Then, 3.00 g (13.5 mmol) of 9,10-bis(chloromethyl)anthracene (1) was added gradually in a crystalline state. The resulting mixture was heated to −10° C. after a lapse of one hour from the completion of this addition and stirred over one night. After the completion of a reaction, DMF was distilled off under a reduced pressure, and the residue was dissolved in 200 ml of methylene chloride and insoluble matter was filtered out. 50 ml of water was added to this, and TFA was added while stirring until the pH of the solution becomes acid. After leaving at rest for 15 minutes, the solution was separated into two layers. A water phase was concentrated by repeating this operation two times and then the water phase was freeze-dried to obtain 2.43 g of quaternary anthracene salt 2 at a yield of 33%. After addition The resulting mixture was heated to −10° C. after a lapse of one hour from the completion of this addition stirred over one night was distilled off under a reduced pressure the residue was dissolved in 200 ml of methylene chloride insoluble matter was filtered out 50 ml of water was added to this, and TFA was added while stirring until the pH of the solution After leaving at rest for 15 minutes the solution was separated into two layers A water phase was concentrated the water phase was freeze-dried