Sodium Cyanide → HCID 11805506, compound

HRID 568179Notes

Reaction equation

HRID 568179 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12]Cl)(=[O:3])[CH3:2].[C-:14]#[N:15].[Na+]>CS(C)=O>[C:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][C:14]#[N:15])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 11458285HCID 11458285, compound

Product 1

HCID 11805506HCID 11805506, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

To a glass-made three-necked flask (volume: 100 ml) with a condenser, 50.0 g of [2-(chloromethyl)phenyl]methyl acetate (purity: 89%) and 50.0 g of dimethyl sulfoxide were added, and the mixture was heated to 80° C. Thereto, 50.0 g of a 34 wt % aqueous sodium cyanide solution was added dropwise while stirring over one hour. After completion of the dropwise addition, the mixed solution was continuously stirred for one hour while keeping the temperature at 80° C. The reaction mixture obtained was analyzed by the gas chromatography. As a result, the amount of [2-(cyano-methyl)phenyl]methyl acetate produced was 34.0 g (180 mmol) and the yield was 80 mol % based on [2-(chloromethyl)-phenyl]methyl acetate. Also, it was verified that 3.6 g (24 mmol) of [2-(hydroxymethyl)phenyl]acetonitrile which is a precursor of 3-isochromanone was produced.

Workup

  1. additionAfter completion of the dropwise addition
  2. stirringthe mixed solution was continuously stirred for one hour
  3. customat 80° C
  4. customThe reaction mixture obtained

Sources & evidence

ORD record
ord-cbda74fa3f7641959b42216670041873
Source dataset
uspto-grants-2001_01
Patent number
US06180801B2

Reaction notes

Loading…