Hydrochloric Acid → 2-Chloro-3-methylbenzoic acid

HRID 1760041Notes

Reaction equation

HRID 1760041 reaction equation
N([O-])=O.[Na+].N[C:6]1[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=[O:9].[ClH:16]>O.[OH-].[Na+].Cl[Cu]>[Cl:16][C:6]1[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=[O:9]

Participants

7

Reactant 3

HCID 313Hydrochloric Acid2×HCID 781012-Amino-3-methylbenzoic acidHCID 23668193Sodium Nitrite

Product 1

HCID 1398792-Chloro-3-methylbenzoic acid

Reagents, catalysts & solvents 3

HCID 62652Cuprous chlorideCatalystHCID 962WaterSolvent2×HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

Sodium nitrite (14.0 g; 0.2 mol) was added to a solution of 2-amino-3-methylbenzoic acid (30.2 g; 0.2 mol) in a mixture of water (200 mL) and NaOH/aq (30%; 24 mL). The solution was cooled to 0° C. and was added dropwise, with stirring, to a mixture of HCl (conc.; 87.6 mL) and ice (100 g). After stirring for a few minutes, the resultant solution was added to an ice cold mixture of HCl/aq (23%; 100 g), CuCl (20 g; 0.2 mol) and water (40 mL). The solution was stirred at room temperature for 30 minutes and at 100° C. for 30 minutes, cooled, and the resultant precipitate was isolated by filtration, was washed with water, and was dried overnight, yielding 27.4 g (80.3%) of a white crystalline material.

Workup

  1. additionwas added dropwise
  2. stirringThe solution was stirred at room temperature for 30 minutes and at 100° C. for 30 minutes
  3. temperaturecooled

Sources & evidence

ORD record
ord-0d3da5f82a2240dc8a2d7dcf3c4304e4
Source dataset
uspto-grants-2005_01
Patent number
US06838478B2

Reaction notes

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