Hydrochloric Acid → HCID 13013688, compound

HRID 894931Notes

Reaction equation

HRID 894931 reaction equation
[Cl:1][C:2]1[CH:17]=[C:16]([N+]([O-])=O)[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9].N([O-])=O.[Na+].[ClH:25]>CN(C)C=O.O>[Cl:1][C:2]1[CH:17]=[C:16]([Cl:25])[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9]

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 13013686HCID 13013686, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 13013688HCID 13013688, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

The product (10 g) from paragraph (a) was dissolved in dimethyl formamide (150 ml), cooled to 5°-10° C. and concentrated hydrochloric acid (40 ml) added dropwise, the temperature being kept at 10°-15° C. The mixture was then kept at 5° C. while sodium nitrite (5.2 g) in water (20 ml) was added dropwise with stirring over a period of 30 minutes. The solution so prepared was added dropwise to a solution of cuprous chloride (19 g) in concentrated hydrochloric acid (150 ml) kept at 10° C., giving a thick green suspension. When addition was complete, the mixture was left to stand overnight and then heated to 60° C. for 30 minutes. The white solid was filtered off, dried, and recrystallised from petroleum (100°-120° C.) to give 3(2,4-dichlorophenoxy)benzoic acid (5.1 g) with a melting point of 143°-144° C. This compound was used as starting material for compound No. 19 of Table 1.

Workup

  1. temperaturecooled to 5°-10° C.
  2. custombeing kept at 10°-15° C
  3. additionwas added dropwise
  4. customThe solution so prepared
  5. customkept at 10° C.
  6. customgiving a thick green suspension
  7. additionWhen addition
  8. waitthe mixture was left
  9. waitto stand overnight
  10. filtrationThe white solid was filtered off
  11. customdried
  12. customrecrystallised from petroleum (100°-120° C.)

Sources & evidence

ORD record
ord-c048a1edf35f4f089e4cf15e7064dd0e
Source dataset
uspto-grants-1981_08
Patent number
US04285723

Reaction notes

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