Benzene → 5-(4-Nitrophenoxy)-salicylic acid

HRID 1973048Notes

Reaction equation

HRID 1973048 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1.[OH-].[Na+].C1C=CC=CC=1>CS(C)=O>[N+:19]([C:16]1[CH:17]=[CH:18][C:13]([O:11][C:8]2[CH:7]=[C:3]([C:4]([OH:6])=[O:5])[C:2]([OH:1])=[CH:10][CH:9]=2)=[CH:14][CH:15]=1)([O-:21])=[O:20]

Participants

6

Reactant 4

HCID 241BenzeneHCID 34692,5-Dihydroxybenzoic acidHCID 74741-Chloro-4-nitrobenzeneHCID 14798Sodium Hydroxide

Product 1

HCID 214925045-(4-Nitrophenoxy)-salicylic acid

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

77 g of 2,5-dihydroxybenzoic acid and 78.5 g of p-chloronitrobenzene were dissolved in 300 ml of dimethyl sulphoxide under a nitrogen atmosphere, and 40 g of sodium hydroxide and 225 ml of benzene were added to the resulting solution. The mixture was then distilled under reflux at 90° to 95° C on a water separator until no more water was separated off (about 2 hours). The benzene was distilled off in a water jet vacuum, the residue poured into 2.5 liters of water, the mixture acidified with concentrated hydrochloric acid while stirring vigorously, the crude, pale brown 5-(4-nitrophenoxy)-salicylic acid which was precipitated was filtered off under suction and washed acid free with water. Drying in vacuo at 80° C gave 126 g (92% of the theoretical yield) of 5-(4-nitrophenoxy)-salicylic acid, recrystallised from methanol (and active carbon, optionally with a little water added) 120 g (87% of the theoretical) of yellow crystals melting at 193° to 194° C.

Workup

  1. distillationThe mixture was then distilled
  2. temperatureunder reflux at 90° to 95° C on a water separator until no more water
  3. customwas separated off (about 2 hours)
  4. distillationThe benzene was distilled off in a water jet vacuum
  5. additionthe residue poured into 2.5 liters of water
  6. customthe crude, pale brown 5-(4-nitrophenoxy)-salicylic acid which was precipitated
  7. filtrationwas filtered off under suction
  8. washwashed acid free with water
  9. customDrying in vacuo at 80° C
  10. customgave 126 g (92% of the

Sources & evidence

ORD record
ord-e0826b83470c4632a7ba50c7be52751c
Source dataset
uspto-grants-1976_12
Patent number
US03996197

Reaction notes

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