Sodium Formate → Benzenamine, 3,3'-(1,3-phenylenebis(oxy))bis-

HRID 2309138Notes

Reaction equation

HRID 2309138 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[O:5][C:6]1[CH:11]=[C:10](Cl)[CH:9]=[C:8]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([NH2:20])[CH:15]=2)[CH:7]=1.C([O-])=O.[Na+]>[Pd].C(O)(C)C>[NH2:20][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=1)[O:13][C:8]1[CH:9]=[CH:10][CH:11]=[C:6]([O:5][C:4]2[CH:21]=[CH:22][CH:23]=[C:2]([NH2:1])[CH:3]=2)[CH:7]=1

Participants

5

Reactant 2

HCID 2723810Sodium FormateHCID 135310493-[3-(3-Aminophenoxy)-5-chlorophenoxy]aniline

Product 1

HCID 66342Benzenamine, 3,3'-(1,3-phenylenebis(oxy))bis-Yield 90.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

Into a glass vessel equipped with a thermometer, a reflux condenser and a stirrer were fed 1,3-bis(3-aminophenoxy)-5-chlorobenzene (8.2 g, 0.025 mol), 5% Pd-C (made by Japan Engelhardt Co.) (0.25 g), sodium formate (4.3 g, 0.063 mol) and 60% aqueous solution of isopropanol (50 ml), and reaction was carried out under reflux with stirring for 5 hours. After completion of the reaction, the catalyst was removed by filtering while hot, followed by cooling to deposit colorless, prismatic crystals, which were filtered and dried to obtain 1,3-bis(3-aminophenoxy)benzene (6.6 g, yield 90.3%). The purity according to high rate liquid chromatography was 99%. M.P.: 105°~107° C.

Workup

  1. customInto a glass vessel equipped with a thermometer, a reflux condenser and a stirrer
  2. temperatureunder reflux
  3. customAfter completion of the reaction
  4. customthe catalyst was removed
  5. filtrationby filtering while hot,
  6. temperatureby cooling
  7. filtrationprismatic crystals, which were filtered
  8. customdried

Sources & evidence

ORD record
ord-1cae63fab62147488d992bdc8d352310
Source dataset
uspto-grants-1987_09
Patent number
US04692554

Reaction notes

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