Sulfuric Acid → 2-(4-Hydroxyphenyl)propanenitrile

HRID 2397230Notes

Reaction equation

HRID 2397230 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:11])[C:9]#[N:10])=[CH:4][CH:3]=1.N([O-])=[O:13].[Na+].S(=O)(=O)(O)O>Cl.O>[OH:13][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:11])[C:9]#[N:10])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 1200112-(4-Aminophenyl)propiononitrileHCID 23668193Sodium Nitrite

Product 1

HCID 895432-(4-Hydroxyphenyl)propanenitrileYield 81%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Procedure

Finely ground 2-(4-aminophenyl) propionitrile (73 g., 0.5 mole) was suspended in concentrated hydrochloric acid (125 ml.). The stirred suspension was diazotised at 0°-5° C. by the dropwise addition of a solution of sodium nitrite (36.23 g., 0.525 mole) in water (60 ml.) during 1- 2 hours. The almost clear solution was stirred for a further 20 minutes at 5°-10° C., then poured into a stirred, boiling solution of concentrated sulphuric acid (250 ml.) in water (2.5 l.). After 6 minutes it was cooled in an ice-bath, then extracted with ether (×4). The combined ether extracts were extracted with 2N-sodium hydroxide (×6). The combined alkaline extracts were cooled in ice-bath, acidified with concentrated hydrochloric acid and extracted with ether (×3). The combined ether extracts were washed with saturated sodium chloride solution (×3), dried (Na2SO4) and evaporated to leave a dark brown oil (66.7 g.) which on distillation gave 2-(4-hydroxyphenyl) propionitrile (59.58 g.), b.p. 112°-122° C./0.125 m.m., m.p. 41°-46° C.

Workup

  1. additionpoured into a stirred
  2. temperatureAfter 6 minutes it was cooled in an ice-bath
  3. extractionextracted with ether (×4)
  4. extractionThe combined ether extracts were extracted with 2N-sodium hydroxide (×6)
  5. temperatureThe combined alkaline extracts were cooled in ice-bath
  6. extractionextracted with ether (×3)
  7. washThe combined ether extracts were washed with saturated sodium chloride solution (×3)
  8. dry with materialdried (Na2SO4)
  9. customevaporated
  10. customto leave a dark brown oil (66.7 g.) which
  11. distillationon distillation

Sources & evidence

ORD record
ord-cddae0c533b747a69537b4c00c54da72
Source dataset
uspto-grants-1977_05
Patent number
US04021440

Reaction notes

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