2,4-Dichlorobenzoic Acid → HCID 762883, compound

HRID 1378554Notes

Reaction equation

HRID 1378554 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1O.[OH-].[Na+]>>[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]1[O:6][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=1

Participants

4

Reactant 3

HCID 57872,4-Dichlorobenzoic AcidHCID 58012-AminophenolHCID 14798Sodium Hydroxide

Product 1

HCID 762883HCID 762883, compound

Conditions

Temperature
140 °C

Procedure

A 2.0 L, three-necked, round-bottomed flask equipped with a mechanical stirrer, a condenser containing a nitrogen inlet valve, and a thermometer was charged with 250 g of 2,4-dichlorobenzoic acid, 157.1 g of 2-aminophenol, and 250 mL of polyphosphoric acid. The mixture was heated under nitrogen for 16 h. The solution was cooled to 140° C. and was poured over a chilled 1M aqueous sodium hydroxide solution. The solid brown precipitate was collected by filtration. The material was then vacuum distilled with a head temperature of 160°-180° C. The solid was recrystallized from toluene and dried in a vacuum oven at 80° C. for 12 h. Yield 257 g (74%); mp=130.6-131.3.

Workup

  1. customA 2.0 L, three-necked, round-bottomed flask equipped with a mechanical stirrer, a condenser
  2. additioncontaining a nitrogen inlet valve
  3. temperatureThe mixture was heated under nitrogen for 16 h
  4. filtrationThe solid brown precipitate was collected by filtration
  5. distillationvacuum distilled with a head temperature of 160°-180° C
  6. customThe solid was recrystallized from toluene
  7. customdried in a vacuum oven at 80° C. for 12 h

Sources & evidence

ORD record
ord-6d1e75baa8384af489cbc43d9f9470d2
Source dataset
uspto-grants-1997_09
Patent number
US05668245

Reaction notes

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