Sodium Cyanide → 3-[4-(2-Hydroxyethyl)phenyl]propionitrile

HRID 225795Notes

Reaction equation

HRID 225795 reaction equation
[C-:1]#[N:2].[Na+].O[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][O:15]S(C2C=CC(C)=CC=2)(=O)=O)=[CH:9][CH:8]=1>CS(C)=O>[OH:15][CH2:14][CH2:13][C:10]1[CH:9]=[CH:8][C:7]([CH2:6][CH2:5][C:1]#[N:2])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 87668833Toluene-4-sulfonic Acid 2-[4-(2-Hydroxyethyl)-phenyl]ethyl Ester

Product 1

HCID 690358473-[4-(2-Hydroxyethyl)phenyl]propionitrileYield 99.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

Sodium cyanide (1.8 g, 37 mmol) was added to a stirred solution of the intermediate from Step B (10 g, 31 mmol) in DMSO (100 mL). The mixture was heated to 60° C. overnight (˜16 hours) and then the DMSO was removed under reduced pressure. DCM (100 mL) was added to the residue and the resulting mixture was washed with water (1×100 mL), saturated NaCl (1×100 mL), dried over magnesium sulfate, filtered and the solvent removed under reduced pressure to provide 5.4 g of the title intermediate (99% yield), which was used without further purification.

Workup

  1. customthe DMSO was removed under reduced pressure
  2. additionDCM (100 mL) was added to the residue
  3. washthe resulting mixture was washed with water (1×100 mL), saturated NaCl (1×100 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-cb7dc7fa077f4313a0f4bcd5bb0ab4e2
Source dataset
uspto-grants-2009_07
Patent number
US07557126B2

Reaction notes

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