m,alpha-Dichlorotoluene → HCID 3402182, compound

HRID 1655354Notes

Reaction equation

HRID 1655354 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[H-].[Na+].[H][H].[Cl:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH2:18]Cl>CN(C=O)C.O>[Cl:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH2:18][O:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 12103m,alpha-DichlorotolueneHCID 130194-CyanophenolHCID 24758Sodium hydrideHCID 178418361HCID 178418361, compound

Product 1

HCID 3402182HCID 3402182, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5×10-2 mole of 4-hydroxy benzonitrile (VIl) in 100 ml of DMF are added little by little 5×10-2 mole of NaH so as to obtain a temperature of 25° C. Then the solution is heated to 50° C. until the release of hydrogen ceases. After cooling to 0 ° C., 5×10-2 of 3-chloro benzyl chloride (VIII) is added little by little. The reaction mixture is heated to 40 ° C. for one hour then poured into 300 ml of iced water. The resultant solid is separated by filtration then recrystallized in an ethanol-water mixture, which leads to the expected compound.

Workup

  1. customto obtain a temperature of 25° C
  2. temperatureThe reaction mixture is heated to 40 ° C. for one hour
  3. customThe resultant solid is separated by filtration
  4. customthen recrystallized in an ethanol-water mixture, which

Sources & evidence

ORD record
ord-16e71209143944ec9dba08d856ad7893
Source dataset
uspto-grants-1993_10
Patent number
US05250551

Reaction notes

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