Sodium Hydroxide → 2-(4-Hydroxy-3-nitrobenzoyl)benzoic acid

HRID 365653Notes

Reaction equation

HRID 365653 reaction equation
Cl[C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]([OH:12])=[O:11])=[O:7])=[CH:4][C:3]=1[N+:19]([O-:21])=[O:20].[OH-:22].[Na+]>O1CCOCC1>[OH:22][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]([OH:12])=[O:11])=[O:7])=[CH:4][C:3]=1[N+:19]([O-:21])=[O:20]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 665622-(4-Chloro-3-nitrobenzoyl)benzoic acid

Product 1

HCID 2257052-(4-Hydroxy-3-nitrobenzoyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-(4-hydroxy-3-nitrobenzoyl)benzoic acid is prepared as follows: a mixture of 10.0 g of 2-(4-chloro-3-nitrobenzoyl)benzoic acid, 200 ml of aqueous sodium hydroxide (1.5 M) and 20 ml of dioxane is heated at reflux for 12 hours. After cooling, the mixture is added to 200 ml of 1:1 concentrated sulfuric acid-ice water with stirring. The resulting solid is filtered, washed with water to a pH of about 6 and dried to obtain 9.5 g of 2-(4-hydroxy-3-nitrobenzoyl)benzoic acid as a light yellow solid. MS: (EI 70 eV); M+,(%): 287 (36); 197 (31); 166 (100); 149 (75); 120 (34).

Workup

  1. custom2-(4-hydroxy-3-nitrobenzoyl)benzoic acid is prepared
  2. temperatureis heated
  3. temperatureat reflux for 12 hours
  4. temperatureAfter cooling
  5. filtrationThe resulting solid is filtered
  6. washwashed with water to a pH of about 6
  7. customdried

Sources & evidence

ORD record
ord-e3adbc2bb6c449e49e3650e7f51c5f30
Source dataset
uspto-grants-2000_10
Patent number
US06127515

Reaction notes

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