Methanol → HCID 13531050, compound

HRID 580686Notes

Reaction equation

HRID 580686 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[CH3:9][O-:10].[Na+].C[N:13]1[CH2:17][CH2:16][CH2:15][C:14]1=O.[Cl:19][C:20]1[CH:25]=[C:24](Cl)[CH:23]=[C:22]([Cl:27])[CH:21]=1.[CH3:28]O>>[ClH:19].[NH2:13][C:17]1[CH:28]=[C:9]([CH:14]=[CH:15][CH:16]=1)[O:10][C:24]1[CH:23]=[C:22]([Cl:27])[CH:21]=[C:20]([O:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([NH2:1])[CH:3]=2)[CH:25]=1

Participants

6

Reactant 5

HCID 887MethanolHCID 79501,3,5-TrichlorobenzeneHCID 115683-AminophenolHCID 13387N-methyl-2-pyrrolidoneHCID 10942334Sodium Methoxide

Product 1

HCID 13531050HCID 13531050, compoundYield 85%

Procedure

120 g (1.1 mol) of 3-aminophenol, 59.5 g (1.1 mol) of sodium methoxide and 500 ml of N-methylpyrrolidone were charged in the same apparatus as described in Example 1. The temperature of the content was raised under stirring while passing gaseous nitrogen through it. When the internal temperature reached 67° C., methanol began to be distilled away. The temperature was raised slowly while distilling away methanol. When the internal temperature reached 120° C., 91 g (0.5 mol) of 1,3,5-trichlorobenzene was added. The amount of methanol distilled away was 38 ml. The content was heated to 170° to 180° C. and maintained at that temperature for 15 hours to accomplish the condensation. Then the reaction mixture was treated according to the same procedure as described in Example 1 to obtain 170 g of 1,3-bis(3-aminophenoxy)-5-chlorobenzene hydrochloride (yield: 85%).

Workup

  1. temperatureThe temperature of the content was raised
  2. customreached 67° C.
  3. distillationto be distilled away
  4. temperatureThe temperature was raised slowly
  5. distillationwhile distilling away methanol
  6. customreached 120° C.
  7. distillationThe amount of methanol distilled away was 38 ml
  8. temperatureThe content was heated to 170° to 180° C.
  9. temperaturemaintained at that temperature for 15 hours
  10. customthe condensation
  11. additionThen the reaction mixture was treated

Sources & evidence

ORD record
ord-be861a6fee28448c950310bec2e8dcbe
Source dataset
uspto-grants-1988_06
Patent number
US04754068

Reaction notes

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