Sodium Chloride → HCID 59463773, compound

HRID 1713342Notes

Reaction equation

HRID 1713342 reaction equation
COC(=O)[CH:4]([C:16]#[N:17])[C:5]1([CH3:15])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[O:8][CH2:7][CH2:6]1.[Cl-].[Na+]>CS(C)=O.O>[CH3:15][C:5]1([CH2:4][C:16]#[N:17])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[O:8][CH2:7][CH2:6]1

Participants

5

Reactant 2

HCID 5234Sodium ChlorideHCID 59463786HCID 59463786, compound

Product 1

HCID 59463773HCID 59463773, compoundYield 69.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of 6 g (23 mmol) of cyano(4-methylchroman-4-yl)acetic acid methyl ester and 7.25 g (124 mmol) of sodium chloride in 40 mL of wet DMSO was warmed to reflux. The reaction was monitored by TLC. After 4 hours, the reaction was cooled and diluted with water and extracted with diethyl ether. The combined organic layers were washed with four portions of water, brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 3 g (68%) of (4-methylchroman-4-yl)acetonitrile as an oil.

Workup

  1. temperaturewas warmed to reflux
  2. temperaturethe reaction was cooled
  3. extractionextracted with diethyl ether
  4. washThe combined organic layers were washed with four portions of water, brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d0317b59637d468e92b7f1d318f86e6d
Source dataset
uspto-grants-2010_09
Patent number
US07795272B2

Reaction notes

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