Sulfuric Acid → 2-(4-Hydroxyphenyl)propanenitrile

HRID 1658140Notes

Reaction equation

HRID 1658140 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 (x4). The combined ether extracts were extracted with 2N-sodium hydroxide solution (x6). The combined alkaline extracts were cooled in ice-bath, acidified with concentrated hydrochloric acid and extracted with ether (x3). The combined ether extracts were washed with saturated sodium chloride solution (x3), 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 (x4)
  4. extractionThe combined ether extracts were extracted with 2N-sodium hydroxide solution (x6)
  5. temperatureThe combined alkaline extracts were cooled in ice-bath
  6. extractionextracted with ether (x3)
  7. washThe combined ether extracts were washed with saturated sodium chloride solution (x3)
  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-947203b9de5e4ab597158e45c34415c9
Source dataset
uspto-grants-1976_06
Patent number
US03962452

Reaction notes

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