Nitric Acid → 2-(4-Nitrophenyl)butyric acid

HRID 249543

Reaction equation

HRID 249543 reaction equation
[N+:1]([O-:4])(O)=[O:2].S(=O)(=O)(O)O.[C:10]1([CH:16]([CH2:20][CH3:21])[C:17]([OH:19])=[O:18])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[N+:1]([C:13]1[CH:14]=[CH:15][C:10]([CH:16]([CH2:20][CH3:21])[C:17]([OH:19])=[O:18])=[CH:11][CH:12]=1)([O-:4])=[O:2]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 70122-Phenylbutyric Acid

Product 1

HCID 240472-(4-Nitrophenyl)butyric acidYield 69%

Procedure

A mixture of concentrated nitric acid (32 mL) and concentrated sulfuric acid (32 mL) were cooled in an ice salt bath. Solid 2-phenylbutyric acid (16.42 g, 100 mmol) was added in small portions maintaining the solution temperature below 10° C. The reaction was warmed to room temperature and allowed to stir for 1 hour. The product was isolated by pouring the reaction mixture onto 150 mL of crushed ice, filtering the white solid and recrystallizing from EtOH to give 14.5 g (69%) of the product as white crystals.

Workup

  1. temperaturewere cooled in an ice salt bath
  2. temperaturemaintaining the solution temperature below 10° C
  3. customThe product was isolated
  4. filtrationfiltering the white solid
  5. customrecrystallizing from EtOH

Sources & evidence

ORD record
ord-dbcbd8d36d6545c49b205f36b43c2e60
Source dataset
uspto-grants-1993_05
Patent number
US05214191

Linked notes

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