1,4-bis(chloromethyl)benzene

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: 34.3 g (0.22 mol) of 4,4′-bipyridyl and 106 g (0.66 mol) of α,α′-dichloro-p-xylene are stirred in 500 ml of acetonitrile at 90° C. for 4 hours under an argon atmosphere. After cooling, the precipitate is filtered off and washed sufficiently with acetonitrile. Drying gives 88.1 g of 1,1′-di[p-(chloromethyl)benzyl]-4,4′-bipyridinium dichloride. After cooling the precipitate is filtered off washed sufficiently with acetonitrile Drying

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

Procedure: 2.8 g Potassium carbonate is added over 3 hours to a mixture of 3.8 g 4-hydroxy-2-isopropylidenecoumaran-3-one, 3.5 g 1,4-bis-(chloromethyl)benzene and 150 ml butanone at 70-75° C. The mixture is refluxed for 16 hours, then filtered, the filtrate evaporated and the residue purified by silica gel chromatography (eluent isohexane/ethyl acetate 3:1) to give 1.3 g of the desired intermediate. The mixture is refluxed for 16 hours filtered the filtrate evaporated the residue purified by silica gel chromatography (eluent isohexane/ethyl acetate 3:1)

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

Procedure: To a mixture of α,α'-dichloro-p-xylene (50 g, 28.6 mmol) and sodium iodide (8.6 g, 57 mmol) in acetone (100 mL) was added tri-n-butylamine (3.7 g, 20.0 mmol). The reaction mixture was stirred at room temperature under argon for several days after which time TLC examination showed completion of the reaction. The reaction mixture was filtered and the solvent was removed under reduced pressure to give an oily residue. The residue was washed with pentane several times and dried to give a yellow solid. The product was used without further purification. completion of the reaction The reaction mixture was filtered the solvent was removed under reduced pressure to give an oily residue The residue was washed with pentane several times dried to give a yellow solid The product was used without further purification

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

Procedure: A mixture of tri-n-butylamine (6 g, 32.2 mmol) and α,α'-dichloro-p-xylene (8.0 g, 46.0 mmol) in methanol (50 mL) was refluxed for 15 h after which time TLC examination showed completion of the reaction. Methanol was removed under reduced pressure to give an oily residue. The colorless oil was washed several times with toluene and hexane and then dried. The product obtained was used without further purification. was refluxed for 15 h after which time TLC examination completion of the reaction Methanol was removed under reduced pressure to give an oily residue The colorless oil was washed several times with toluene and hexane dried The product obtained was used without further purification

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

Procedure: A mixture of tri-n-butylphosphine (7 g, 34.6 mmol, leq.) in toluene (50 mL) was added dropwise to a mixture of α,α'-dichloro-p-xylene (12.1 g, 69.8 mmol, 2 eq.) in toluene (200 mL) under argon gas. The reaction mixture was allowed to stir for 12 hours at room temperature under argon, after which time the tri-n-butylphosphonium chloride salt had crystallized out of solution. The crystals were filtered and washed several times with toluene and hexanes, then air dried: 1H NMR (CDCl3) δ0.92 (t, 9H), 1.44 (m, 12H), 2.39 (m, 6H), 4.35-4.40 (d, 2H), 4.56 (s, 2H), 7.36-7.39 (d, 2H) , 7.47-7.51 (dd, 2H). after which time the tri-n-butylphosphonium chloride salt had crystallized out of solution The crystals were filtered washed several times with toluene and hexanes air dried

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of p-hydroxybenzoic acid benzyl ester (68.4 g, 0.3 mol) in N,N-dimethylformamide (274 g) sodium carbonate (15.9 g, 0.15 mol) was added, and stirred at 100° C. Then, p-xylylenedichloride (26.2 g, 0.15 mol) was added to the reaction mixture in 10 minutes, and stirred at 100° C. for one hour. Water was added to the resultant to separate a clued precipitate. The precipitate was filtered, added to N,N-dimethylformamide to be dissolved at 90° C., cooled, filtered, and dried to give a white crystal of 1,4-bis(p-carbobenzyloxyphenoxymethyl)benzene (27.8 g, yield 33.0): m.p. 154°-157° C. stirred at 100° C. for one hour to separate a clued precipitate The precipitate was filtered added to N,N-dimethylformamide to be dissolved at 90° C. cooled filtered dried

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

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

Procedure: A mixture of tri-n-butylamine (6 g, 32.2 mmol) and α,α'-dichloro-p-xylene (8 g, 46.0 mmol) in methanol (50 mL) was refluxed for 15 h after which time TLC examination showed completion of the reaction. Methanol was removed under reduced pressure to give an oily residue. The colorless oil was washed several times with toluene and hexane and then dried. The product obtained was used without further purification. was refluxed for 15 h after which time TLC examination completion of the reaction Methanol was removed under reduced pressure to give an oily residue The colorless oil was washed several times with toluene and hexane dried The product obtained was used without further purification

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

Procedure: A mixture of tri-n-butylamine (6 g, 32.2 mmol) and α,α'-dichloro-p-xylene (8 g, 46.0 mmol) in methanol (50 mL) was refluxed for 15 h after which time TLC examination showed completion of the reaction. Methanol was removed under reduced pressure to give an oily residue. The colorless oil was washed several times with toluene and hexane and then dried. The product obtained was used without further purification. was refluxed for 15 h after which time TLC examination completion of the reaction Methanol was removed under reduced pressure to give an oily residue The colorless oil was washed several times with toluene and hexane dried The product obtained was used without further purification

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

Procedure: A mixture of tri-n-butylphosphine (7 g, 34.6 mmol, 1 eq.) in toluene (50 mL) was added dropwise to a mixture of α,α'-dichloro-p-xylene (12.1 g, 69.2 mmol, 2 eq.) in toluene (200 mL) under argon gas. The reaction mixture was allowed to stir for 12 hours at room temperature under argon, after which time the tri-n-butylphosphonium chloride salt had crystallized out of solution. The crystals were filtered and washed several times with toluene and hexanes, then air dried: 1H NMR (CDCl3) δ 0.92 (t, 9H), 1.44 (m, 12H), 2.39 (m, 6H), 4.35-4.40 (d, 2H), 4.56 (s, 2H), 7.36-7.39 (d, 2H), 7.47-7.51 (dd, 2H). after which time the tri-n-butylphosphonium chloride salt had crystallized out of solution The crystals were filtered washed several times with toluene and hexanes air dried