Sulfuric Acid → 891657-51-5

HRID 547277Notes

Reaction equation

HRID 547277 reaction equation
N[C:2]1[CH:3]=[C:4]([CH:8]([CH3:11])[C:9]#[N:10])[CH:5]=[CH:6][CH:7]=1.[OH:12]S(O)(=O)=O.N([O-])=O.[Na+].C(OCC)(=O)C>O>[OH:12][C:2]1[CH:3]=[C:4]([CH:8]([CH3:11])[C:9]#[N:10])[CH:5]=[CH:6][CH:7]=1

Participants

6

Conditions

Temperature
4 °C

Procedure

2-(3-aminophenyl)propionitrile (1.0 g, 6.75 mmol), was suspended in water (12 mL), then under vigorous stirring, H2SO4 (1.5 ml, 27 mmol) was added dropwise. After stirring 20 min, the mixture was cooled to 4° C., a solution of NaNO2 (0.466 g, 6.75 mmol) in water (5 mL) was added dropwise and the resulting solution was left stirring at reflux 1 h. After cooling at room temperature, ethyl acetate (10 mL) was added to the mixture, the crude was extracted and the organic phase washed with water (3×10 mL) and brine (3×10 mL). After drying over Na2SO4 and solvent evaporation under reduced pressure 2-(3-hydroxyphenyl)propionitrile was obtained as yellow oil in nearly quantitative yield.

Workup

  1. waitthe resulting solution was left
  2. stirringstirring
  3. temperatureat reflux 1 h
  4. temperatureAfter cooling at room temperature
  5. extractionthe crude was extracted
  6. washthe organic phase washed with water (3×10 mL) and brine (3×10 mL)
  7. dry with materialAfter drying over Na2SO4 and solvent evaporation under reduced pressure 2-(3-hydroxyphenyl)propionitrile
  8. customwas obtained as yellow oil in nearly quantitative yield

Sources & evidence

ORD record
ord-6a71d20463354bff8c3df10618465825
Source dataset
uspto-grants-2011_05
Patent number
US07939521B2

Reaction notes

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