Nitric Acid → 3(R)-(4-nitrophenyl)butanoic acid

HRID 1357856Notes

Reaction equation

HRID 1357856 reaction equation
[C:1]1([C@H:7]([CH3:12])[CH2:8][C:9]([OH:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O.[N+:18]([O-])([OH:20])=[O:19]>O>[N+:18]([C:4]1[CH:5]=[CH:6][C:1]([C@H:7]([CH3:12])[CH2:8][C:9]([OH:11])=[O:10])=[CH:2][CH:3]=1)([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 852992(3R)-3-phenylbutanoic acid

Product 1

HCID 541618043(R)-(4-nitrophenyl)butanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(R)-3-phenylbutanoic acid (10.0 g) was added to concentrated sulphuric acid (40 mL) at −5° C. under nitrogen. The resulting thick gel-like mixture was stirred vigorously and fuming nitric acid (2.8 mL) was added slowly over 20 minutes. The reaction mixture was poured onto a mixture of ice and water (500 mL) and the resulting white precipitate was collected by filtration, then washed thoroughly with water, and then dried to give the title compound (10.1 g) as a white solid.

Workup

  1. filtrationthe resulting white precipitate was collected by filtration
  2. washwashed thoroughly with water
  3. customdried

Sources & evidence

ORD record
ord-9f4a8f80140440f19ca0f2accf3509d4
Source dataset
uspto-grants-2003_07
Patent number
US06593354B2

Reaction notes

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