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1.a
1,2-dicyano-4,5-diethylbenzene (2.3g, 12mmol) was stirred with heating in 75% sulfuric acid (30 ml) at 150°C for 3.5 hrs. The reaction solution was poured into ice-cold water. The precipitated crystals were collected by filtration, washed with water, and dissolved in 10% aqueous sodium hydroxide solution. The insoluble materials were separated by filtration, and the resulting filtrate was made acid with concentrated hydrochloric acid. The precipitated crystals were collected by filtration, washed with water, and dried to give 1.5 g of 4,5-diethylphthalic acid.
With sulfuric acid; water at 150℃; for 3.5h;
1.a
(a) 4,5-Diethylphthalic acid 1,2-dicyano-4,5-diethylbenzene (2.3g, 12mmol) was stirred with heating in 75% sulfuric acid (30 ml) at 150°C for 3.5 hrs. The reaction mixture was poured into ice-cold water. The precipitated crystals were collected by filtration, washed with water, and dissolved in 10% aqueous sodium hydroxide solution. The insoluble materials were separated by filtration, and the resulting filtrate was made acidic with concentrated hydrochloric acid. The precipitated crystals were collected by filtration, washed with water, and dried to give 1.5 g of 4,5-diethylphthalic acid.(b) 4,5-diethylphthalic anhydride.
hexaammonium heptamolybdate tetrahydrate[ No CAS ]
[ 96563-12-1 ]
2,3,9,10,16,17,23,24-octaethylphthalocyanatomanganese(II)[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
0%
With I2 In neat (no solvent) a mixt. of ligand, Mn, I2 and (NH4)6Mo7O24*4H2O were heated to 220°C under N2, mixt. was slowly heated to 340°C over a 40 min period; mixt. was cooled, solid was slowly heated to 480°C in vac. to give sublimed product (monitored by UV/VIS);
bis(2,3,9,10,16,17,23,24-octaethylphthalocyanine)europium(III)[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
53%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In further solvent(s) mixt. of 4,5-diethylphthalodinitrile and Eu compd. in isoamyl alcohol heated, 1,8-diazabicyclo(5.4.0)undec-7-ene added, mixt. refluxed under a stream of Ar; dild. with CHCl3, filtered, filtrate evapd. to dryness (distn.), aq. MeOH added to residue, mixt. refluxed, filtered, dried under vac., dissolved in C6H6, column chromy. (silica gel, C6H6), preparative TLC (alumina, C6H6);
bis(2,3,9,10,16,17,23,24-octaethylphthalocyanine)europium(III)[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
26%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In further solvent(s) mixt. of 4,5-diethylphthalodinitrile and Eu compd. in isoamyl alcohol heated, 1,8-diazabicyclo(5.4.0)undec-7-ene added, mixt. refluxed under a stream of Ar; dild. with CHCl3, filtered, filtrate evapd. to dryness (distn.), aq. MeOH added to residue, mixt. refluxed, filtered, dried under vac., dissolved in C6H6, column chromy. (silica gel, C6H6), preparative TLC (alumina, C6H6);
bis(2,3,9,10,16,17,23,24-octaethylphthalocyanine)dysprosium(III)[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
15%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In further solvent(s) mixt. of 4,5-diethylphthalodinitrile and Dy compd. in isoamyl alcohol heated, 1,8-diazabicyclo(5.4.0)undec-7-ene added, mixt. refluxed under a stream of Ar; dild. with CHCl3, filtered, filtrate evapd. to dryness (distn.), aq. MeOH added to residue, mixt. refluxed, filtered, dried under vac., dissolved in C6H6, column chromy. (silica gel, C6H6), preparative TLC (alumina, C6H6);
bis(2,3,9,10,16,17,23,24-octaethylphthalocyanine)lutetium(III)[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
11%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In further solvent(s) mixt. of 4,5-diethylphthalodinitrile and Lu compd. in isoamyl alcohol heated, 1,8-diazabicyclo(5.4.0)undec-7-ene added, mixt. refluxed under a stream of Ar; dild. with CHCl3, filtered, filtrate evapd. to dryness (distn.), aq. MeOH added to residue, mixt. refluxed, filtered, dried under vac., dissolved in C6H6, column chromy. (silica gel, C6H6), preparative TLC (alumina, C6H6);
lutetium(III) acetylacetonate trihydrate[ No CAS ]
[ 96563-12-1 ]
bis(2,3,9,10,16,17,23,24-octaethylphthalocyanine)lutetium(III)[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
21%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In further solvent(s) mixt. of 4,5-diethylphthalodinitrile and Lu compd. in isoamyl alcohol heated, 1,8-diazabicyclo(5.4.0)undec-7-ene added, mixt. refluxed under a stream of Ar; dild. with CHCl3, filtered, filtrate evapd. to dryness (distn.), aq. MeOH added to residue, mixt. refluxed, filtered, dried under vac., dissolved in C6H6, column chromy. (silica gel, C6H6), preparative TLC (alumina, C6H6);
tris(acetylacetonato)dysprosium(III) trihydrate[ No CAS ]
[ 96563-12-1 ]
bis(2,3,9,10,16,17,23,24-octaethylphthalocyanine)dysprosium(III)[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
33%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In further solvent(s) mixt. of 4,5-diethylphthalodinitrile and Dy compd. in isoamyl alcohol heated, 1,8-diazabicyclo(5.4.0)undec-7-ene added, mixt. refluxed under a stream of Ar; dild. with CHCl3, filtered, filtrate evapd. to dryness (distn.), aq. MeOH added to residue, mixt. refluxed, filtered, dried under vac., dissolved in C6H6, column chromy. (silica gel, C6H6), preparative TLC (alumina, C6H6);