2,6-Dichloro-4-methylbenzamide → 2,6-Dichloro-4-methylbenzoic acid

HRID 280647Notes

Reaction equation

HRID 280647 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([Cl:12])[C:3]=1[C:4](N)=[O:5].N([O-])=[O:14].[Na+]>C(O)(=O)C.O>[Cl:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([Cl:12])[C:3]=1[C:4]([OH:14])=[O:5]

Participants

5

Reactant 2

HCID 136496812,6-Dichloro-4-methylbenzamideHCID 23668193Sodium Nitrite

Product 1

HCID 136496822,6-Dichloro-4-methylbenzoic acidYield 83%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

A stirred 0° C. solution of 2,6-dichloro-4-methylbenzamide (8.6 g, 42. mmol) in 2:1 (v/v) acetic acid-concentrated hydrochloric acid (165 ml) was treated dropwise with a solution of sodium nitrite (19.0 g, 275 mmol) in water (42 ml). The mixture was stirred 30 minutes at 5° C., slowly warmed to 85° C., and kept 1 hour. The mixture was cooled, concentrated under vacuum, and treated with cold water (50 ml). The product was filtered, washed twice with cold water, and dried 16 hours at 50° C. over phosphorus pentoxide under vacuum to provide 7.15 g (83%) of 2,6-dichloro-4-methylbenzoic acid, m.p. 139°-145° C.

Workup

  1. temperatureslowly warmed to 85° C.
  2. waitkept 1 hour
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated under vacuum
  5. additiontreated with cold water (50 ml)
  6. filtrationThe product was filtered
  7. washwashed twice with cold water
  8. dry with materialdried 16 hours at 50° C. over phosphorus pentoxide under vacuum

Sources & evidence

ORD record
ord-5de876d13bf949b6ac098e6c9861422b
Source dataset
uspto-grants-1986_05
Patent number
US04590201

Reaction notes

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