Hydrochloric Acid → 2-Chloro-6-hydroxybenzoic acid

HRID 1885966Notes

Reaction equation

HRID 1885966 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7](N)[C:8]=1[C:9]([OH:11])=[O:10].Cl.N([O-])=[O:15].[Na+]>O>[Cl:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([OH:15])[C:8]=1[C:9]([OH:11])=[O:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23668193Sodium NitriteHCID 53444447HCID 53444447, compound

Product 1

HCID 925912-Chloro-6-hydroxybenzoic acidYield 44.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
5 °C

Procedure

A stirred suspension of 10.0 grams (0.048 mole) of 6-chloroanthranilic acid hydrochloride and 100 mL of concentrated hydrochloric acid in 200 mL of water was cooled to 5° C., and a solution of 3.5 grams (0.050 mole) of sodium nitrite in 50 mL of water was added dropwise during a 10 minute period. Upon completion of addition, the reaction mixture was warmed to 90° C. where it was stirred for about 10 minutes. The reaction mixture was cooled to ambient temperature and was filtered. The filter cake was washed with cold heptane and dried to yield 3.7 grams of 6-chlorosalicylic acid. The nmr spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition
  2. temperaturethe reaction mixture was warmed to 90° C. where it
  3. temperatureThe reaction mixture was cooled to ambient temperature
  4. filtrationwas filtered
  5. washThe filter cake was washed with cold heptane
  6. customdried

Sources & evidence

ORD record
ord-4fc6ca6a540947d78b46c25c4aec1019
Source dataset
uspto-grants-1992_09
Patent number
US05149357

Reaction notes

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