Hydrochloric Acid → 3-(2-hydroxyethoxy)benzonitrile

HRID 1516614Notes

Reaction equation

HRID 1516614 reaction equation
C([O:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]#[N:15])[CH:9]=1)(=O)C.Cl>CO.O1CCCC1.[OH-].[Li+]>[OH:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][CH:13]=1)[C:14]#[N:15]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 68593387HCID 68593387, compound

Product 1

HCID 122221843-(2-hydroxyethoxy)benzonitrile

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3939Lithium HydroxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-(3-Cyanophenoxy)ethyl acetate (3.01 g, 14.7 mmol) obtained in Step 1 was dissolved in a mixed solvent of methanol and tetrahydrofuran (1:1), and 2N lithium hydroxide solution (14.7 ml) was added under ice-cooling. The mixture was stirred at room temperature for 45 min, 3N hydrochloric acid (10 ml) was added under ice-cooling, and the mixture was concentrated under reduced pressure. The residue was diluted with ethyl acetate, and the mixture was washed with 1N hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution, and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel chromatography (hexane:ethyl acetate 85:15-55:45) to give the title compound.

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. temperaturecooling
  4. concentrationthe mixture was concentrated under reduced pressure
  5. additionThe residue was diluted with ethyl acetate
  6. washthe mixture was washed with 1N hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution, and saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customThe obtained residue was purified by silica gel chromatography (hexane:ethyl acetate 85:15-55:45)

Sources & evidence

ORD record
ord-1d86ff2e913746559387e111c968ad79
Source dataset
uspto-grants-2012_07
Patent number
US08227506B2

Reaction notes

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