3-Hydroxybenzoic Acid → HCID 13013686, compound

HRID 894930Notes

Reaction equation

HRID 894930 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[Cl:11][C:12]1[CH:13]=[C:14]([N+:19]([O-:21])=[O:20])[CH:15]=[CH:16][C:17]=1Cl.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:11][C:12]1[CH:13]=[C:14]([N+:19]([O-:21])=[O:20])[CH:15]=[CH:16][C:17]=1[O:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 74203-Hydroxybenzoic AcidHCID 74431,2-Dichloro-4-nitrobenzeneHCID 11430Potassium Carbonate

Product 1

HCID 13013686HCID 13013686, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-hydroxybenzoic acid (5 g), dimethyl formamide (50 ml), 3,4-dichloronitrobenzene (7 g) and anhydrous potassium carbonate (10 g) was stirred and heated at 100° C. for 14 hours. The solvent was removed under reduced pressure and the residue poured into water and acidified with 2 molar hydrochloric acid. The yellow solid which separated was recrystallised from toluene to give the required benzoic acid derivative (8.0 g) with a melting point of 172°-173° C.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue poured into water
  3. customThe yellow solid which separated
  4. customwas recrystallised from toluene

Sources & evidence

ORD record
ord-1a7a1a2fc73e45de840dfb10d48b0509
Source dataset
uspto-grants-1981_08
Patent number
US04285723

Reaction notes

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