Formic Acid → HCID 54053211, compound

HRID 1080565Notes

Reaction equation

HRID 1080565 reaction equation
[Cl:1][CH:2]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH2:14][CH3:15])=[CH:8][CH:7]=1)C#N.[CH:16]([OH:18])=[O:17].Cl>O>[Cl:1][CH:2]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH2:14][CH3:15])=[CH:8][CH:7]=1)[C:16]([OH:18])=[O:17]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 313Hydrochloric AcidHCID 53646989HCID 53646989, compound

Product 1

HCID 54053211HCID 54053211, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The α-chloro-β-p-butylphenylpropionitrile 2 (166 g, 0.750 moles) was stirred over 240 mL formic acid and 160 mL concentrated HCl at reflux for 16 h. The reaction mixture was cooled, diluted with 300 mL water and washed with ethyl acetate. The ethyl acetate solution was washed with water, saturated aqueous NaCl, dried over Na2SO4, filtered and concentrated under reduced pressure. The bulk oil solidified on standing. The solid was recrystallized twice from hexane, yielding 139.0 g (0.58 moles, 77% yield) of a white solid, mp. 52.7°-53.6° C.

Workup

  1. temperatureat reflux for 16 h
  2. temperatureThe reaction mixture was cooled
  3. washwashed with ethyl acetate
  4. washThe ethyl acetate solution was washed with water, saturated aqueous NaCl
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe solid was recrystallized twice from hexane

Sources & evidence

ORD record
ord-1e3b3c773f0044a59dc76164600fa62c
Source dataset
uspto-grants-1996_12
Patent number
US05582814

Reaction notes

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