Hydrochloric Acid → 3,5-Dinitro-4-phenylbenzoic acid

HRID 1605541Notes

Reaction equation

HRID 1605541 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([N+:20]([O-:22])=[O:21])[C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:7]([O:9]C)=[O:8])([O-:3])=[O:2].Cl>COCCO.[OH-].[Na+].O>[N+:1]([C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([N+:20]([O-:22])=[O:21])[C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:7]([OH:9])=[O:8])([O-:3])=[O:2]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 21546857Methyl 3,5-dinitro-4-phenylbenzoate

Product 1

HCID 124087663,5-Dinitro-4-phenylbenzoic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 80192-MethoxyethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a stirred suspension of methyl 3,5-dinitro-4-phenylbenzoate (145 g) in 2-methoxyethanol (1.5 l), 2 N sodium hydroxide (300 ml) is added dropwise during about 30 minutes. After additional stirring for about 15 minutes, the resulting solution is acidified by the dropwise addition of 4 N hydrochloric acid (250 ml), and the mixture is thereafter diluted with water (about 3 l). After cooling, the resulting precipitate is collected by filtration, washed with water and dried. After recrystallization from aqueous ethanol, 3,5-dinitro-4-phenylbenzoic acid is obtained with a melting point of 219°-221° C.

Workup

  1. additionis added dropwise during about 30 minutes
  2. temperatureAfter cooling
  3. filtrationthe resulting precipitate is collected by filtration
  4. washwashed with water
  5. customdried
  6. customAfter recrystallization from aqueous ethanol

Sources & evidence

ORD record
ord-4c8168bf01524a988dc6f94f110ccbc7
Source dataset
uspto-grants-1976_04
Patent number
US03950380

Reaction notes

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